[1-[(Benzyloxy)methyl]cyclopropyl]methanol

Base Information

• Chemical Name: [1-[(Benzyloxy)methyl]cyclopropyl]methanol
• CAS No.: 177200-76-9
• Molecular Formula: C12H16O2
• Molecular Weight: 192.258
• European Community (EC) Number: 879-676-1
• Mol file: 177200-76-9.mol

Synonyms:177200-76-9;[1-[(Benzyloxy)methyl]cyclopropyl]methanol;(1-((benzyloxy)methyl)cyclopropyl)methanol;{1-[(benzyloxy)methyl]cyclopropyl}methanol;1-benzyloxymethyl-1-(hydroxymethyl)cyclopropane;[1-(phenylmethoxymethyl)cyclopropyl]methanol;MFCD26398597;1-[(Phenylmethoxy)methyl]cyclopropanemethanol;SCHEMBL3488328;KBGZAPJNEFMKKZ-UHFFFAOYSA-N;CHA20076;AKOS023401908;AS-82515;SY333328;DB-337108;CS-0110095;EN300-1223467;A1-23223;F2147-3621

Chemical Property of [1-[(Benzyloxy)methyl]cyclopropyl]methanol

Chemical Property:

• PSA: 29.46000
• LogP: 1.97570
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 192.115029749
• Heavy Atom Count: 14
• Complexity: 169

Purity/Quality:

99% ^*data from raw suppliers

[1-[(Benzyloxy)methyl]cyclopropyl]methanol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC1(CO)COCC2=CC=CC=C2
• Uses: [1-[(Benzyloxy)methyl]cyclopropyl]methanol is an protected intermediate used in the synthesis of Montelukast (M568000), a selective leukotriene D4-receptor antagonist used as an antiasthmatic agent.

Technology Process of [1-[(Benzyloxy)methyl]cyclopropyl]methanol

There total 3 articles about [1-[(Benzyloxy)methyl]cyclopropyl]methanol 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: 79.0%

[1-(hydroxymethyl)cyclopropyl]methanol (39590-81-3) + benzyl bromide (100-39-0) → {1-[(benzyloxy)methyl]cyclopropyl}methanol (177200-76-9)

Guidance literature:

[1-(hydroxymethyl)cyclopropyl]methanol; With sodium hydride; In N,N-dimethyl-formamide; at -10 ℃; for 0.166667h;

benzyl bromide; In N,N-dimethyl-formamide; at 20 ℃; for 3h; Further stages.;

DOI:10.1021/ol006085q

Reference yield: 57.0%

[1-(hydroxymethyl)cyclopropyl]methanol (39590-81-3) + 1-phenyl-2-bromoethane (103-63-9) → {1-[(benzyloxy)methyl]cyclopropyl}methanol (177200-76-9)

Guidance literature:

[1-(hydroxymethyl)cyclopropyl]methanol; With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 0.25h;

1-phenyl-2-bromoethane; In N,N-dimethyl-formamide; at 20 ℃; for 24h;

Reference yield:

diethyl cyclopropane-1,1-dicarboxylate (1559-02-0) → {1-[(benzyloxy)methyl]cyclopropyl}methanol (177200-76-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 99 percent / LiAlH₄ / tetrahydrofuran / 16 h / Heating

2.1: NaH / dimethylformamide; various solvent(s) / 0.17 h / -10 °C

2.2: 79 percent / dimethylformamide; various solvent(s) / 3 h / 20 °C

With lithium aluminium tetrahydride; sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; 1.1: Reduction / 2.1: Metallation / 2.2: Addition;

DOI:10.1021/ol006085q

upstream raw materials:

[1-(hydroxymethyl)cyclopropyl]methanol

benzyl bromide

diethyl cyclopropane-1,1-dicarboxylate

1-phenyl-2-bromoethane

Downstream raw materials:

1-[(phenylmethoxy)methyl]cyclopropanecarboxaldehyde

1-({1-[(benzyloxy)methyl]cyclopropyl}methyl)-4-bromo-5-(4-fluorophenyl)-3-methyl-1H-pyrazole

1-((benzyloxy)methyl)cyclopropane-1-carboxylic acid

1-({1-[(benzyloxy)methyl]cyclopropyl}methyl)-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Refernces

• 1、 -. "PANTETHENOYLCYSTEINE DERIVATIVES AND USES THEREOF". Paragraph 3278. . Retrieved 2020/10/20.
• 2、 -. "SUBSTITUTED TRICYCLICS AND METHOD OF USE". Paragraph 1265. . Retrieved 2017/02/09.