Tetrahydrofuran → 4-Bromo-6-(cyclohexylmethyl)-1,2,3,5-tetrahydro-s-indacene
Reaction equation
[Br:1][C:2]1[C:13]2[CH2:12][CH2:11][CH2:10][C:9]=2[CH:8]=[C:7]2[C:3]=1[CH2:4][CH:5]([CH2:15][CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1)[C:6]2=O.C1COCC1.[BH4-].[Na+]>CO>[Br:1][C:2]1[C:3]2[CH2:4][C:5]([CH2:15][CH:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)=[CH:6][C:7]=2[CH:8]=[C:9]2[C:13]=1[CH2:12][CH2:11][CH2:10]2Participants
Procedure
To a solution of 39.5 g (0.114 mol) of 4-bromo-2-(cyclohexylmethyl)-3,5,6,7-tetrahydro-s-indacen-1(2H)-one in 170 ml of THF 15.2 g (0.398 mol) of NaBH4 was added. Further on, 340 ml of methanol was added dropwise by vigorous stirring for 2 h. The resulting mixture was stirred for 12 h at room temperature, evaporated to a volume of ca. 300 ml, and then 100 ml of 3.0 M HCl was added. The product was extracted with 3×200 ml of dichloromethane. The organic extract was dried over Na2SO4 and then evaporated to dryness. A solution of the residue and 1.4 g of TsOH in 800 ml of toluene was refluxed for 30 min with Dean-Stark head. The obtained solution was passed through short layer (50 mm) of silica gel 60 (40-63 um), the filtrate was evaporated to dryness. This procedure gave 34.7 g (93%) of the title product which was further used without an additional purification.
Workup
- stirringThe resulting mixture was stirred for 12 h at room temperature
- customevaporated to a volume of ca. 300 ml
- addition100 ml of 3.0 M HCl was added
- extractionThe product was extracted with 3×200 ml of dichloromethane
- extractionThe organic extract
- dry with materialwas dried over Na2SO4
- customevaporated to dryness
- temperatureA solution of the residue and 1.4 g of TsOH in 800 ml of toluene was refluxed for 30 min with Dean-Stark head
- customthe filtrate was evaporated to dryness
Sources & evidence
- ORD record
- ord-463166bd0a7346f8b6d77411f09f6aa0
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08865848B2
Reaction notes
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