Hydrofluoric Acid → 3-(5-Hydroxypent-1-yl)cyclopentene

HRID 1789545Notes

Reaction equation

HRID 1789545 reaction equation
CC([Si](C)(C)[O:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH:12]1[CH2:16][CH2:15][CH:14]=[CH:13]1)(C)C.F.C(=O)(O)[O-].[Na+]>C(#N)C>[OH:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH:12]1[CH2:16][CH2:15][CH:14]=[CH:13]1

Participants

5

Reactant 3

HCID 14917Hydrofluoric AcidHCID 516892Sodium BicarbonateHCID 139240733-(5-[(1,1-Dimethylethyl)dimethylsiloxy]pent-1-yl)cyclopentene

Product 1

HCID 150530153-(5-Hydroxypent-1-yl)cyclopentene

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3-(5-[(1,1-Dimethylethyl)dimethylsiloxy]pent-1-yl)cyclopentene (300 g, 1.170 moles) is diluted with acetonitrile (3000 ml) and a 40% stock solution of hydrofluoric acid (166 ml) is added. The reaction is stirred at room temperature for 10 minutes and then slowly neutralized with a saturated solution of sodium bicarbonate. The reaction is partitioned between ether (1500 ml) and the aqueous phase extracted with ether (1×1000 ml). The organic layers are combined and the solvent volume is reduced under vacuum. The residue is dried over anhydrous sodium sulfate and the remaining solvent removed leaving a clear, colorless oil. The product is kugelrohred under vacuum leaving a product sufficiently pure for the next reaction (171 g, 1.11 moles).

Workup

  1. customThe reaction is partitioned between ether (1500 ml)
  2. extractionthe aqueous phase extracted with ether (1×1000 ml)
  3. dry with materialThe residue is dried over anhydrous sodium sulfate
  4. customthe remaining solvent removed
  5. customleaving a clear, colorless oil
  6. customleaving a product
  7. customsufficiently pure for the next reaction (171 g, 1.11 moles)

Sources & evidence

ORD record
ord-44bfa0d5f31a44aa9684818b80bf5a65
Source dataset
uspto-grants-1987_08
Patent number
US04689345

Reaction notes

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