Tetrahydrofuran → HCID 69492806, compound

HRID 396591Notes

Reaction equation

HRID 396591 reaction equation
[S:1]1[C:5]([C:6]2[C:7]([O:36][CH3:37])=[CH:8][C:9]([O:34][CH3:35])=[C:10]([CH:12]=[CH:13][C:14]([CH:16]3[C:21](C)(C)[C:20]([O:24][CH3:25])=[C:19](C(C)(C)C)[C:18]([O:30][CH3:31])=[C:17]3O[SiH3])=[O:15])[CH:11]=2)=[CH:4][C:3]2[CH:38]=[CH:39][CH:40]=[CH:41][C:2]1=2.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[O:60]1CCCC1>>[S:1]1[C:5]([C:6]2[C:7]([O:36][CH3:37])=[CH:8][C:9]([O:34][CH3:35])=[C:10]([CH:12]=[CH:13][C:14]([C:16]3[CH:21]=[C:20]([O:24][CH3:25])[C:19]([OH:60])=[C:18]([O:30][CH3:31])[CH:17]=3)=[O:15])[CH:11]=2)=[CH:4][C:3]2[CH:38]=[CH:39][CH:40]=[CH:41][C:2]1=2

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 178493945HCID 178493945, compound

Product 1

HCID 69492806HCID 69492806, compoundYield 46%

Procedure

To a solution of 3-[5-(benzo[b]thien-2-yl)2,4-dimethoxyphenyl]-1-(4-tert-butyldimethyl-siloxy-3,5-dimethoxyphenyl)-2-propen-1-one, from Ex-59B, (0.135 g, 0.228 mmol) in tetrahydrofuran (2 mL) was added tetrabutylammonium fluoride (0.061 g. 0.228 mmol), and the mixture was stirred at room temperature for two hours. Upon quenching with water, the mixture was extracted with dichloromethane. The organic phase was dried and evaporated. Silica gel chromatography (hexane/ethyl acetate, 1:1) gave 0.05 g (46%) of the desired 3-[5-(benzo[b]thien-2-yl)2,4-dimethoxyphenyl]-1-(4-hydroxy-3,5-dimethoxy-phenyl)-2-propen 1-one product as a yellow solid, m.p. 85-105° C.

Workup

  1. customUpon quenching with water
  2. extractionthe mixture was extracted with dichloromethane
  3. customThe organic phase was dried
  4. customevaporated

Sources & evidence

ORD record
ord-2319167470c74286bc7f337014fa2181
Source dataset
uspto-grants-2003_08
Patent number
US06608101B1

Reaction notes

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