Water → HCID 18961588, compound

HRID 1707544Notes

Reaction equation

C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:7][O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[CH:11][C:10]=1[CH3:18].Cl[CH2:20][S:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.O>CN(C=O)C>[CH3:7][O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([O:15][CH2:20][S:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:14])=[CH:11][C:10]=1[CH3:18]

Participants

Conditions

Temperature: 65 °C

Procedure

Cesium carbonate (13.00 g, 40.0 mmol) is added to a solution of 4-methoxy-3-methyl benzoic acid (6.65 g, 40.0 mmol) in dry DMF (50 ml) at ambient temperature. The mixture is stirred at 65° C. for 20 minutes and cooled to 0° C., before chloromethyl phenylsulfide (5.76 g, 36 mmol) in dry DMF (10 ml) is added dropwise. Stirring is continued at 0° C. for 30 minutes, then at ambient temperature for 2 hours and finally at 70° C. for 1 hour, before water is added and the product extracted into diethyl ether. The ether solution is washed with 1M sodium hydroxide and 4 times with brine, dried (MgSO4) and evaporated. The crude product is used in Intermediate 8 without further purification.

Workup

additionis added dropwise
stirringStirring
waitis continued at 0° C. for 30 minutes
waitat ambient temperature for 2 hours
waitfinally at 70° C. for 1 hour
extractionthe product extracted into diethyl ether
washThe ether solution is washed with 1M sodium hydroxide and 4 times with brine
dry with materialdried (MgSO4)
customevaporated
customThe crude product is used in Intermediate 8 without further purification

Sources & evidence

ORD record: ord-d3ffbb1ebbb14b9c86b8bc2dac7c5b27
Source dataset: uspto-grants-1994_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05354549

Reaction notes

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