Fluoride Ion → HCID 9795641, compound

HRID 585721Notes

Reaction equation

HRID 585721 reaction equation
[C:1]([O:5][CH2:6][CH:7]1[CH2:12][CH2:11][CH:10]([C:13]2[CH:18]=[CH:17][C:16]([O:19][Si](C(C)(C)C)(C)C)=[CH:15][C:14]=2[O:27][Si](C(C)(C)C)(C)C)[CH2:9][CH2:8]1)(=[O:4])[CH2:2][CH3:3].[F-]>CO>[C:1]([O:5][CH2:6][CH:7]1[CH2:8][CH2:9][CH:10]([C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][C:14]=2[OH:27])[CH2:11][CH2:12]1)(=[O:4])[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 28179Fluoride IonHCID 69801944HCID 69801944, compound

Product 1

HCID 9795641HCID 9795641, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of [4-(2,4-Bis{[tert-butyl(dimethyl)silyl]oxy}phenyl)cyclohexyl]methyl propionate (110 mg), methanol (10 ml) and Amberlyst fluoride resin (0.4 g) were stirred at room temperature for 72 hr. The reaction mixture was filtered, and the filtrate was evaporated in vacuo. The residue was purified by flash column chromatography (SiO2, ethyl acetate/petrol, 1:2 v/v) to give the title compound as a cream solid and a mixture of diastereoisomers (44 mg, 73%). δH (CDCl3) 1.17 (3H, t), 1.38-2.14 (9H, m), 2.34-2.40 (2H, q), 2.64-2.80 (1H, m), 3.96 (0.6H, d), 4.20 (0.4H, d), 5.10-5.24 (2H, m), 6.28-6.33 (1H, m), 6.36-6.40 (1H, m), 6.98 (1H, dd); m/z (ES+) 279 (M+H)+.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate was evaporated in vacuo
  3. customThe residue was purified by flash column chromatography (SiO2, ethyl acetate/petrol, 1:2 v/v)

Sources & evidence

ORD record
ord-3bd5371381604aae97528ddafee7da45
Source dataset
uspto-grants-2005_08
Patent number
US06933319B2

Reaction notes

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