HCID 11018798, compound → HCID 10519016, compound

HRID 1078506Notes

Reaction equation

C[S-].[Li+].CCOCC.CCCCCC.[C:15]([C:19]1[CH:20]=[C:21]([C:26]([CH3:37])=[CH:27][C:28]2[CH:36]=[CH:35][C:31]([C:32]([OH:34])=[O:33])=[CH:30][CH:29]=2)[CH:22]=[CH:23][C:24]=1[OH:25])([CH3:18])([CH3:17])[CH3:16]>CN(C=O)C>[C:15]([C:19]1[CH:20]=[C:21](/[C:26](/[CH3:37])=[CH:27]/[C:28]2[CH:29]=[CH:30][C:31]([C:32]([OH:34])=[O:33])=[CH:35][CH:36]=2)[CH:22]=[CH:23][C:24]=1[OH:25])([CH3:18])([CH3:16])[CH3:17]

Participants

Conditions

Temperature: 120 °C

Procedure

1.84 g of lithium methanethiolate are added to 2 g (5.67 mmol) of the E ester obtained in Example 33(b) in 40 ml of DMF. The reaction mixture is stirred under nitrogen at 120° C. for 4 h. After the same treatment as in Example 8, followed by a chromatography in the ether/hexane eluent (80/20), 1.69 g of a mixture of E and Z isomers of 4-[-2-(3-tert-butyl-4-hydroxyphenyl)propenyl]benzoic acid are isolated in the respective proportions (83:17). A recrystallization from the hexane/ether mixture gives 225 mg of the expected derivative which melts at 209° C.

Workup

customare isolated in the respective proportions (83:17)
customA recrystallization from the hexane/ether mixture
customgives 225 mg of the expected derivative which melts at 209° C.

Sources & evidence

ORD record: ord-5af5a44a7ede42a3ac1bf619b190edc3
Source dataset: uspto-grants-1996_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05547983

Reaction notes

Loading…