Methyl Glycolate → [4-(1-{4-[2-(tert-Butyl-dimethyl-silanyloxy)-3,3-dimethyl-butoxy]-3-methyl-phenyl}-1-ethyl-propyl)-2-methyl-benzyloxy]-acetic acid methyl ester

HRID 230819Notes

Reaction equation

HRID 230819 reaction equation
[C:1]([Si:5]([CH3:36])([CH3:35])[O:6][CH:7]([C:31]([CH3:34])([CH3:33])[CH3:32])[CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([C:21]2[CH:26]=[CH:25][C:24]([CH2:27][OH:28])=[C:23]([CH3:29])[CH:22]=2)([CH2:19][CH3:20])[CH2:17][CH3:18])=[CH:12][C:11]=1[CH3:30])([CH3:4])([CH3:3])[CH3:2].[C:37]([O:41][CH3:42])(=[O:40])[CH2:38]O>C1(C)C=CC=CC=1>[CH3:42][O:41][C:37](=[O:40])[CH2:38][O:28][CH2:27][C:24]1[CH:25]=[CH:26][C:21]([C:16]([C:13]2[CH:14]=[CH:15][C:10]([O:9][CH2:8][CH:7]([O:6][Si:5]([C:1]([CH3:3])([CH3:2])[CH3:4])([CH3:35])[CH3:36])[C:31]([CH3:34])([CH3:33])[CH3:32])=[C:11]([CH3:30])[CH:12]=2)([CH2:19][CH3:20])[CH2:17][CH3:18])=[CH:22][C:23]=1[CH3:29]

Participants

4

Reactant 2

HCID 66774Methyl GlycolateHCID 57763514[4-(1-{4-[2-(t-Butyldimethylsilanyloxy)-3,3-dimethylbutoxy]-3-methylphenyl}-1-ethylpropyl)-2-methylphenyl]methanol

Product 1

HCID 57763463[4-(1-{4-[2-(tert-Butyl-dimethyl-silanyloxy)-3,3-dimethyl-butoxy]-3-methyl-phenyl}-1-ethyl-propyl)-2-methyl-benzyloxy]-acetic acid methyl esterYield 40%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of enantiomer 1 of [4-(1-{4-[2-(tert-butyl-dimethyl-silanyloxy)-3,3-dimethyl-butoxy]-3-methyl-phenyl}-1-ethyl-propyl)-2-methyl-phenyl]-methanol, (2.10 g, 4.10 mmol) and PhCH3 (10 mL) is added methyl glycolate (6.5 mL, 81.89 mmol) and MeReO3 (0.02 g, 0.082 mmol). The solution is heated at a reflux for 2 hours with the use of a Dean-Stark trap. The solution is concentrated and chromatographed to give the title compound (0.96 g, 1.64 nmol, 40%).

Workup

  1. temperatureThe solution is heated at
  2. temperaturea reflux for 2 hours with the use of a Dean-Stark trap
  3. concentrationThe solution is concentrated
  4. customchromatographed

Sources & evidence

ORD record
ord-0e7bcac8511d4b3b9c51985c2eba5819
Source dataset
uspto-grants-2009_07
Patent number
US07566803B2

Reaction notes

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