Water → HCID 19353123, compound

HRID 378215Notes

Reaction equation

HRID 378215 reaction equation
B.[CH3:2][C:3]1([CH3:28])[CH2:12][CH2:11][C:10]([CH3:14])([CH3:13])[C:9]2[CH:8]=[C:7]([C:15]3([CH3:27])[C:19]4[CH:20]=[C:21]([C:24](O)=[O:25])[CH:22]=[CH:23][C:18]=4[O:17][CH2:16]3)[CH:6]=[CH:5][C:4]1=2.O>C1COCC1>[CH3:2][C:3]1([CH3:28])[CH2:12][CH2:11][C:10]([CH3:13])([CH3:14])[C:9]2[CH:8]=[C:7]([C:15]3([CH3:27])[C:19]4[CH:20]=[C:21]([CH2:24][OH:25])[CH:22]=[CH:23][C:18]=4[O:17][CH2:16]3)[CH:6]=[CH:5][C:4]1=2

Participants

5

Reactant 3

HCID 962WaterHCID 6331BoraneHCID 15840104HCID 15840104, compound

Product 1

HCID 19353123HCID 19353123, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

7.7 ml of a 1M solution of borane in THF are added dropwise at 0° C. to a solution of 3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-3-methyl-2,3-dihydrobenzofuran-5-carboxylic acid (1.7 g, 4.7 mol) in THF (10 ml). The mixture is stirred for 4 hours at ambient temperature and then 2 ml of a solution of THF and water (1:1) are added. After concentration in vacuo at 40° C. in a rotary evaporator. The mixture is extracted with ethyl acetate. The organic phase is washed with water, dried over anhydrous magnesium sulphate, concentrated in vacuo at 40° C. in a rotary evaporator. The product is purified by flash chromatography on a silica column.

Workup

  1. concentrationAfter concentration in vacuo at 40° C.
  2. customin a rotary evaporator
  3. extractionThe mixture is extracted with ethyl acetate
  4. washThe organic phase is washed with water
  5. dry with materialdried over anhydrous magnesium sulphate
  6. concentrationconcentrated in vacuo at 40° C. in a rotary evaporator
  7. customThe product is purified by flash chromatography on a silica column

Sources & evidence

ORD record
ord-58f918dc2c8f4784b10556de01a32966
Source dataset
uspto-grants-2000_02
Patent number
US06030952

Reaction notes

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