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

HRID 1532846Notes

Reaction equation

HRID 1532846 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

7

Reactant 5

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 159702-Thiopheneacetic acidHCID 5462977Diethyl azodicarboxylateHCID 10824066Methyl 4-hydroxymethyl-2-phenylbenzoate

Product 1

HCID 865867894-Thioacetoxymethyl-2-phenylbenzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent4×

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

  1. customat ambient temperature
  2. customThe mixture is evaporated
  3. customthe solvent is evaporated
  4. customthe residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-adbb225228dc418ebfd97eea11a6f463
Source dataset
uspto-grants-2001_03
Patent number
US06204293B1

Reaction notes

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