Methanol → Methyl 2,2-dimethyl-4-(2-hydroxyethyl)-8-(t-butyldimethylsiloxy)octanoate

HRID 465566Notes

Reaction equation

HRID 465566 reaction equation
[CH3:1][C:2]1(C)[CH2:9][CH:8]([CH2:10][CH2:11][CH2:12][CH2:13][O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])[CH2:7][CH2:6][O:5][C:3]1=O.[CH3:23][O-:24].[Na+].[CH3:26][OH:27]>>[CH3:1][C:2]([CH3:3])([CH2:9][CH:8]([CH2:7][CH2:6][OH:5])[CH2:10][CH2:11][CH2:12][CH2:13][O:14][Si:15]([C:18]([CH3:19])([CH3:20])[CH3:21])([CH3:16])[CH3:17])[C:23]([O:27][CH3:26])=[O:24]

Participants

4

Reactant 3

HCID 887MethanolHCID 99966312,2-Dimethyl-4-(4-t-butyldimethylsilyloxybutyl)epsilon-caprolactoneHCID 10942334Sodium Methoxide

Product 1

HCID 14986673Methyl 2,2-dimethyl-4-(2-hydroxyethyl)-8-(t-butyldimethylsiloxy)octanoate

Procedure

To a solution of 2.35 g (7.2 mmol) of 2,2-dimethyl-4-(4-t-butyldimethylsilyloxybutyl)epsilon-caprolactone in 22 ml methanol is added 0.386 g (7.2 mmol) sodium methoxide and the mixture is stirred for 2.5 h. The reaction is quenched with saturated aqueous ammonium chloride and extracted twice with methylene chloride. The combined organic extracts are washed with water and brine, dried, filtered and evaporated to yield methyl 2,2-dimethyl-4-(2-hydroxyethyl)-8-(t-butyldimethylsilyloxy)-octanoate as an oil; NMR (CDCl3): delta 3.67 (s,3H), 3.55-3.65 (m,4H), 1.18 (s,6H), 0.89 (s,9H).

Workup

  1. customThe reaction is quenched with saturated aqueous ammonium chloride
  2. extractionextracted twice with methylene chloride
  3. washThe combined organic extracts are washed with water and brine
  4. customdried
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-e4612f2cd3d146ce90fc3f8fb5e514e3
Source dataset
uspto-grants-1992_10
Patent number
US05153214

Reaction notes

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