Water → HCID 19353123, compound

HRID 1602710Notes

Reaction equation

HRID 1602710 reaction equation
B.[CH3:2][C:3]1([C:15]2[CH:24]=[CH:23][C:22]3[C:21]([CH3:26])([CH3:25])[CH2:20][CH2:19][C:18]([CH3:28])([CH3:27])[C:17]=3[CH:16]=2)[C:7]2[CH:8]=[C:9]([C:12](O)=[O:13])[CH:10]=[CH:11][C:6]=2[O:5][CH2:4]1.O>C1COCC1>[CH3:25][C:21]1([CH3:26])[CH2:20][CH2:19][C:18]([CH3:27])([CH3:28])[C:17]2[CH:16]=[C:15]([C:3]3([CH3:2])[C:7]4[CH:8]=[C:9]([CH2:12][OH:13])[CH:10]=[CH:11][C:6]=4[O:5][CH2:4]3)[CH:24]=[CH:23][C:22]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

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

Workup

  1. concentrationAfter concentration
  2. customon a rotary evaporator under vacuum at 40° C
  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 on a rotary evaporator under vacuum at 40° C
  7. customThe product is purified by flash chromatography on a column of silica

Sources & evidence

ORD record
ord-9323fa6fb4a5495db95e4d12023f18a6
Source dataset
uspto-grants-1999_11
Patent number
US05981776

Reaction notes

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