Technology Process of 3-benzyloxy-5-hydroxymethyl-2,6,6-trimethyl-cyclohexa-1,4-dienecarboxylic acid methyl ester
There total 9 articles about 3-benzyloxy-5-hydroxymethyl-2,6,6-trimethyl-cyclohexa-1,4-dienecarboxylic acid methyl ester which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone;
In
methanol; acetonitrile;
at 20 ℃;
for 27h;
DOI:10.1039/b005533f
- Guidance literature:
-
Multi-step reaction with 8 steps
1.1: NaH / tetrahydrofuran / 1 h / 20 °C
1.2: tetrahydrofuran / 15 h / 20 °C
2.1: TPAP; NMO; molecular sieves 4 Angstroem / CH2Cl2 / 1 h / 20 °C
3.1: LDA / tetrahydrofuran / -78 °C
3.2: Benzoyl chloride / tetrahydrofuran / 0.92 h / -78 - 20 °C
3.3: SmI2; DMPU / tetrahydrofuran / 1 h / 20 °C
4.1: 66 percent / toluene / 24 h / 150 °C
5.1: 86 percent / tetrahydrofuran / 1 h / 20 °C
6.1: i-BuOCOCl; NEt3 / CH2Cl2 / 2 h / 20 °C
7.1: 87 percent / NCS; NEt3; H2O / tetrahydrofuran / 1 h / 0 °C
8.1: 73 percent / DMPU / acetonitrile; methanol / 27 h / 20 °C
With
1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; N-chloro-succinimide; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; water; sodium hydride; triethylamine; lithium diisopropyl amide; isobutyl chloroformate;
In
tetrahydrofuran; methanol; dichloromethane; toluene; acetonitrile;
1.1: Metallation / 1.2: Etherification / 2.1: Oxidation / 3.1: Metallation / 3.2: Substitution / 3.3: Oxidation / 4.1: Cycloaddition / 5.1: Ring cleavage / 6.1: Cyclization / 7.1: Chlorination / 8.1: Ring cleavage;
DOI:10.1039/b005533f
- Guidance literature:
-
Multi-step reaction with 6 steps
1.1: LDA / tetrahydrofuran / -78 °C
1.2: Benzoyl chloride / tetrahydrofuran / 0.92 h / -78 - 20 °C
1.3: SmI2; DMPU / tetrahydrofuran / 1 h / 20 °C
2.1: 66 percent / toluene / 24 h / 150 °C
3.1: 86 percent / tetrahydrofuran / 1 h / 20 °C
4.1: i-BuOCOCl; NEt3 / CH2Cl2 / 2 h / 20 °C
5.1: 87 percent / NCS; NEt3; H2O / tetrahydrofuran / 1 h / 0 °C
6.1: 73 percent / DMPU / acetonitrile; methanol / 27 h / 20 °C
With
1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; N-chloro-succinimide; water; triethylamine; lithium diisopropyl amide; isobutyl chloroformate;
In
tetrahydrofuran; methanol; dichloromethane; toluene; acetonitrile;
1.1: Metallation / 1.2: Substitution / 1.3: Oxidation / 2.1: Cycloaddition / 3.1: Ring cleavage / 4.1: Cyclization / 5.1: Chlorination / 6.1: Ring cleavage;
DOI:10.1039/b005533f
