Tetrahydrofuran → 4-[2-(1-Hydroxymethyl-cyclopropylmethoxy)-3,4-dimethoxy-phenyl]-indan-1-one
Reaction equation
[Si](CO[C:20]1([CH2:23][O:24][C:25]2[C:30]([O:31][CH3:32])=[C:29]([O:33][CH3:34])[CH:28]=[CH:27][C:26]=2[C:35]2[CH:43]=[CH:42][CH:41]=[C:40]3[C:36]=2[CH2:37][CH2:38][C:39]3=[O:44])[CH2:22][CH2:21]1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.O.O.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[O:66]1CCC[CH2:67]1>>[OH:66][CH2:67][C:20]1([CH2:23][O:24][C:25]2[C:30]([O:31][CH3:32])=[C:29]([O:33][CH3:34])[CH:28]=[CH:27][C:26]=2[C:35]2[CH:43]=[CH:42][CH:41]=[C:40]3[C:36]=2[CH2:37][CH2:38][C:39]3=[O:44])[CH2:22][CH2:21]1Participants
4
Reactant 3
Product 1
Procedure
To a stirring solution of 4-(2-((1-((tert-butyldiphenylsilyl)methoxy)cyclopropyl)methoxy)-3,4-dimethoxyphenyl)-2,3-dihydro-1H-inden-1-one (5 g, 6.25 mmol) in tetrahydrofuran, was added tetrabutylammonium fluoride trihydrate (33 mL, 33 mmol) and the resultant reaction mixture was stirred at RT for 16 h. The reaction mixture was quenched with water and extracted with ethyl acetate (3×). The combined ethyl acetate layer was washed with brine, dried over anhydrous sodium sulphate and concentrated under reduced pressure. Purification was done by column chromatography (silica gel, 0-40% ethyl acetate in pet ether) to afford the title compound as a yellow solid.
Workup
- customthe resultant reaction mixture
- customThe reaction mixture was quenched with water
- extractionextracted with ethyl acetate (3×)
- washThe combined ethyl acetate layer was washed with brine
- dry with materialdried over anhydrous sodium sulphate
- concentrationconcentrated under reduced pressure
- customPurification
Sources & evidence
- ORD record
- ord-594a496276cc4c2a982159f607125e6e
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09051290B2
Reaction notes
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