Potassium Carbonate → 4-Thioacetoxymethyl-2-phenylbenzoic acid methyl ester

HRID 383105Notes

Reaction equation

C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.[S:32]1C=C[CH:34]=[C:33]1CC(O)=O.[CH3:41][O:42][C:43](=[O:58])[C:44]1[CH:49]=[CH:48][C:47]([CH2:50][OH:51])=[CH:46][C:45]=1[C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1.C([O-])([O-])=O.[K+].[K+]>C1COCC1>[CH3:41][O:42][C:43](=[O:58])[C:44]1[CH:49]=[CH:48][C:47]([CH2:50][O:51][C:33](=[S:32])[CH3:34])=[CH:46][C:45]=1[C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To triphenylphosphine (1.2 equivalents) in THF at −78° C. is added diethylazodicarboxylate (1.2 equivalents) in THF. After 10 min thiolacetic acid (1.3 equivalents) in THF is added followed by the resultant compound from Example 16B (1. equivalent) in THF. The reaction is stirred at −78° C. for 1 h and then at ambient temperature until it is judged to be complete by TLC analysis. The mixture is evaporated and the residue is taken up in methanol and is treated with K2CO3 (2 equivalents). When the reaction is judged to be complete by TLC analysis, the solvent is evaporated and the residue is chromatographed on silica gel to afford the title product.

Workup

customat ambient temperature
customThe mixture is evaporated
customthe solvent is evaporated
customthe residue is chromatographed on silica gel

Sources & evidence

ORD record: ord-a049f528cf374ed1a302b0d230a63fa0
Source dataset: uspto-grants-2001_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06310095B1

Reaction notes

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