Water → 2-(1-Triethylsilanyloxy-cyclopentyl)-ethanol

HRID 400220Notes

Reaction equation

HRID 400220 reaction equation
[CH:1]([C:3]1([O:8][Si:9]([CH2:14][CH3:15])([CH2:12][CH3:13])[CH2:10][CH3:11])[CH2:7][CH2:6][CH2:5][CH2:4]1)=[CH2:2].B.[OH2:17]>C1COCC1>[CH2:12]([Si:9]([CH2:10][CH3:11])([CH2:14][CH3:15])[O:8][C:3]1([CH2:1][CH2:2][OH:17])[CH2:7][CH2:6][CH2:5][CH2:4]1)[CH3:13]

Participants

5

Reactant 3

HCID 962WaterHCID 6331BoraneHCID 189444931-Vinyl-1-triethylsilanyloxy-cyclopentane

Product 1

HCID 189444682-(1-Triethylsilanyloxy-cyclopentyl)-ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-Vinyl-1-triethylsilanyloxy-cyclopentane (9.06 g; 40.0 mmole) was dissolved in dry THF (100 ml); at 0° C. borane (1M in THF; 40.0 ml; 40.0 mmole) was added dropwise and the reaction mixture was stirred for one hour at ambient temperature. At 0° C. water (50 ml)was added dropwise, followed by NaBO3.4H2O (7.69 g; 50.0 mmole) and the mixture was stirred for additional 16 hours at ambient temperature; after filtration the organic layer was removed and concentrated in vacuo; the aqu. layer was extracted with tert.-BuOMe (2×50 ml); all organic layers were combined, washed with sat. aqu. NaCl (50 ml) and dried over MgSO4. After filtration the solvent was removed in vacuo, the crude product was chromatographed on silica gel (hexane:ethyl acetate--4:1). 2-(1-Triethylsilanyloxy-cyclopentyl)-ethanol (D1) was obtained as colourless oil.

Workup

  1. stirringthe mixture was stirred for additional 16 hours at ambient temperature
  2. filtrationafter filtration the organic layer
  3. customwas removed
  4. concentrationconcentrated in vacuo
  5. extractionlayer was extracted with tert
  6. washwashed with sat. aqu
  7. dry with materialNaCl (50 ml) and dried over MgSO4
  8. filtrationAfter filtration the solvent
  9. customwas removed in vacuo
  10. customthe crude product was chromatographed on silica gel (hexane:ethyl acetate--4:1)

Sources & evidence

ORD record
ord-5f0295fdf44943dd8087ea9516ea0373
Source dataset
uspto-grants-1998_10
Patent number
US05827883

Reaction notes

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