Triethylamine → (S)-(+)-2,2-Dimethyl-5-oxo-1,3-dioxolane-4-acetic Acid, Tert-butyldiphenylsilyl Ester

HRID 2214489Notes

Reaction equation

HRID 2214489 reaction equation
[CH3:1][C:2]1([CH3:12])[O:6][C@@H:5]([CH2:7][C:8]([OH:10])=[O:9])[C:4](=[O:11])[O:3]1.C(N(CC)CC)C.[C:20]([Si:24](Cl)([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([CH3:23])([CH3:22])[CH3:21]>ClCCl.C1(C)C=CC=CC=1>[CH3:1][C:2]1([CH3:12])[O:6][C@@H:5]([CH2:7][C:8]([O:10][Si:24]([C:20]([CH3:23])([CH3:22])[CH3:21])([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:9])[C:4](=[O:11])[O:3]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 94078tert-ButyldiphenylchlorosilaneHCID 641720(S)-2-(2,2-Dimethyl-5-oxo-1,3-dioxolan-4-yl)acetic acid

Product 1

HCID 86587276(S)-(+)-2,2-Dimethyl-5-oxo-1,3-dioxolane-4-acetic Acid, Tert-butyldiphenylsilyl EsterYield 99.8%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of (S)-(+)-2,2-dimethyl-5-oxo-1,3-dioxolane-4-acetic acid (2.08 g, 11.9 mmol) in dry dichloromethane (20 ml) was treated with triethylamine (1.83 ml, 13.1 mmol) followed by a solution of t-butylchlorodiphenylsilane (3.44 g, 12.5 mmol) in dichloromethane (5 ml) added dropwise over 5 minutes. After 3 hours at 22° C., the reaction mixture was diluted with toluene (250 ml) washed with water, saturated sodium bicarbonate, brine and dried over magnesium sulfate. Evaporation of the solvent under reduced pressure and chromatography of the residue on silica gel (4×12 cm) using a mixture of toluene and ethyl acetate (0–2%) as eluent gave 4.90 g (99% yield) of the title material as a clear oil. 1H NMR (400 MHz, CDCl3) δ: 1.13 (s, 9), 1.58 (s, 3), 3.05 (m, 2), 4.79 (dd, 1, J=4, 7), 7.4–7.8 (m, 10).

Workup

  1. additionadded dropwise over 5 minutes
  2. washwashed with water, saturated sodium bicarbonate, brine
  3. dry with materialdried over magnesium sulfate
  4. customEvaporation of the solvent under reduced pressure and chromatography of the residue on silica gel (4×12 cm)
  5. additiona mixture of toluene and ethyl acetate (0–2%) as eluent

Sources & evidence

ORD record
ord-02373f8e9f6a4a2db7099b41eaba9614
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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