Fluoride Ion → HCID 9795641, compound

HRID 2307182Notes

Reaction equation

HRID 2307182 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-afc8e780a5c34f56a0cc67faeb3a02f0
Source dataset
uspto-grants-2004_12
Patent number
US06828460B2

Reaction notes

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