Glycolic Acid → HCID 22003743, compound

HRID 339787Notes

Reaction equation

[Si:1]([O:8]CC(Cl)=O)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:13]([OH:17])(=[O:16])[CH2:14]O.[Si](OCl)(C(C)(C)C)(C)C.N1C=CN=C1>>[Si:1]([O:8][O:17][C:13](=[O:16])[CH3:14])([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:2])[CH3:3]

Participants

Reactant 4

HCID 757Glycolic Acid

HCID 795Imidazole

HCID 10932700Acetyl chloride, [[(1,1-dimethylethyl)dimethylsilyl]oxy]-

HCID 19793901HCID 19793901, compound

Product 1

HCID 22003743HCID 22003743, compound

Procedure

Scheme I shows the preparation of tert-butyldimethylsilyloxy acetyl chloride. Glycolic acid on reaction with TBDMS-Cl (tert-butyldimethylsilyloxy chloride) in the presence of imidazole provided O-tert-butyldimethylsilyloxy acetic acid, which on reaction with oxalyl chloride gave the desired acid chloride derivative.

Sources & evidence

ORD record: ord-f4bfa73632f44dbeb9cde3a57843e20e
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08895569B2

Reaction notes

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