Tetrabutylammonium Fluoride → (1S,2S)-2-Hydroxy-2-methyl-3-cyclopentene-1-methanol

HRID 222192Notes

Reaction equation

HRID 222192 reaction equation
[Si]([O:18][CH2:19][C@H:20]1[C@@:24]([CH3:26])([OH:25])[CH:23]=[CH:22][CH2:21]1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[OH:18][CH2:19][C@H:20]1[C@@:24]([CH3:26])([OH:25])[CH:23]=[CH:22][CH2:21]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 58944685HCID 58944685, compound

Product 1

HCID 58944597(1S,2S)-2-Hydroxy-2-methyl-3-cyclopentene-1-methanolYield 92.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (1S,5S)-5-({[tert-butyl(diphenyl)silyl]oxy}methyl)-1-methylcyclopent-2-en-1-ol (560 mg, 1.53 mmol) in THF (29.5 mL) at 0° C. was added 1.00 M of tetra-n-butylammonium fluoride in THF (3.06 mL, 3.06 mmol). The mixture was stirred at rt for 2 h, at which point the solvent was concentrated in vacuo and the residue was purified by silica gel chromatography eluting with a gradient of 50 to 100% EtOAc in hexanes to afford the title compound (181 mg, 92%). LC/MS: Rt=0.76 min, ES+ 129 (AA standard).

Workup

  1. concentrationwas concentrated in vacuo
  2. customthe residue was purified by silica gel chromatography
  3. washeluting with a gradient of 50 to 100% EtOAc in hexanes

Sources & evidence

ORD record
ord-0e5951ddf0cc433ab69c1ba361311797
Source dataset
uspto-grants-2012_06
Patent number
US08207177B2

Reaction notes

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