2-(tert-butyldimethylsiloxymethyl)-4-hydroxymethyl-1,3,3-trimethyl-cyclohexa-1,4-diene

Base Information

• Chemical Name: 2-(tert-butyldimethylsiloxymethyl)-4-hydroxymethyl-1,3,3-trimethyl-cyclohexa-1,4-diene
• CAS No.: 595568-54-0
• Molecular Formula: C₁₇H₃₂O₂Si
• Molecular Weight: 296.525
• Mol file: 595568-54-0.mol

Synonyms:2-(tert-butyldimethylsiloxymethyl)-4-hydroxymethyl-1,3,3-trimethyl-cyclohexa-1,4-diene

Chemical Property of 2-(tert-butyldimethylsiloxymethyl)-4-hydroxymethyl-1,3,3-trimethyl-cyclohexa-1,4-diene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(tert-butyldimethylsiloxymethyl)-4-hydroxymethyl-1,3,3-trimethyl-cyclohexa-1,4-diene

There total 12 articles about 2-(tert-butyldimethylsiloxymethyl)-4-hydroxymethyl-1,3,3-trimethyl-cyclohexa-1,4-diene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

2,2-dimethyl-1,3-cyclohexanedione (562-13-0) → 2-(tert-butyldimethylsiloxymethyl)-4-hydroxymethyl-1,3,3-trimethyl-cyclohexa-1,4-diene (595568-54-0)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 88 percent / (+/-)-camphor-10-sulfonic acid / benzene / 0.5 h / Heating

2.1: LiHMDS / hexane; tetrahydrofuran / 1 h / -78 °C

2.2: 89 percent / hexane; tetrahydrofuran / 3.5 h / -78 - 20 °C

3.1: hydrazine hydrate; triethylamine / ethanol / 312 h / Heating

4.1: 9.2 g / DBN; I₂ / diethyl ether / 0.5 h / 20 °C

5.1: t-BuLi / pentane; tetrahydrofuran / 0.5 h / -78 °C

5.2: pentane; tetrahydrofuran / 1.67 h / -78 - 20 °C

6.1: CeCl₃*7H₂O; NaBH₄ / methanol / 0.5 h / 0 °C

7.1: 2.75 g / HCl / H₂O / 0.5 h / 20 °C

8.1: 92 percent / imidazole / CH₂Cl₂ / 14 h / 20 °C

9.1: 87 percent / CH₂Cl₂ / 16 h / 26 °C

10.1: n-BuLi / hexane; tetrahydrofuran / 1 h / -78 °C

10.2: hexane; tetrahydrofuran / 1.67 h / -78 - 20 °C

11.1: 718 mg / CeCl₃*7H₂O; NaBH₄ / methanol / 0.5 h / 0 °C

With 1H-imidazole; hydrogenchloride; sodium tetrahydroborate; n-butyllithium; cerium(III) chloride; 2,6-dichloro-benzonitrile; camphor-10-sulfonic acid; iodine; tert.-butyl lithium; hydrazine hydrate; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; water; pentane; benzene; 6.1: Luche reduction / 11.1: Luche reduction;

DOI:10.1016/S0040-4020(03)00699-9

Reference yield:

5-(tert-butyl-dimethyl-silanyloxymethyl)-4,6,6-trimethyl-cyclohexa-1,4-dienecarbaldehyde (595568-62-0) → 2-(tert-butyldimethylsiloxymethyl)-4-hydroxymethyl-1,3,3-trimethyl-cyclohexa-1,4-diene (595568-54-0)

Guidance literature:

With sodium tetrahydroborate; cerium(III) chloride; In methanol; at 0 ℃; for 0.5h;

DOI:10.1016/S0040-4020(03)00699-9

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → 2-(tert-butyldimethylsiloxymethyl)-4-hydroxymethyl-1,3,3-trimethyl-cyclohexa-1,4-diene (595568-54-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 92 percent / imidazole / CH₂Cl₂ / 14 h / 20 °C

2.1: 87 percent / CH₂Cl₂ / 16 h / 26 °C

3.1: n-BuLi / hexane; tetrahydrofuran / 1 h / -78 °C

3.2: hexane; tetrahydrofuran / 1.67 h / -78 - 20 °C

4.1: 718 mg / CeCl₃*7H₂O; NaBH₄ / methanol / 0.5 h / 0 °C

With 1H-imidazole; sodium tetrahydroborate; n-butyllithium; cerium(III) chloride; In tetrahydrofuran; methanol; hexane; dichloromethane; 4.1: Luche reduction;

DOI:10.1016/S0040-4020(03)00699-9

upstream raw materials:

5-(tert-butyl-dimethyl-silanyloxymethyl)-4,6,6-trimethyl-cyclohexa-1,4-dienecarbaldehyde

2,2-dimethyl-1,3-cyclohexanedione

tert-butyldimethylsilyl chloride

3-Hydroxymethyl-2,2,4-trimethyl-cyclohex-3-enone

Downstream raw materials:

(4S)-2-(tert-butyldimethylsiloxymethyl)-4-hydroxy-4-(hydroxymethyl)-1,3,3-trimethyl-cyclohex-1-ene

(4S,5R)-2-(tert-butyldimethylsiloxymethyl)-4,6-dihydroxy-4-benzoyloxymethyl-1,3,3-trimethyl-cyclohex-1-ene

(4S)-2-(tert-butyldimethylsiloxymethyl)-4,6-dihydroxy-4-benzoyloxymethyl-1,3,3-trimethyl-cyclohex-1-ene

(5S)-3-(tert-butyldimethylsiloxymethyl)-5-hydroxy-5-benzoyloxymethyl-2,4,4-trimethyl-cyclohex-2-en-1-one