Water → HCID 69274730, compound

HRID 271383Notes

Reaction equation

HRID 271383 reaction equation
[CH2:1]([O:8][CH:9]1[CH2:14][CH2:13][CH:12]([O:15][CH2:16][CH:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[OH:18])[CH:11]([F:25])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.[Si:35](OS(C(F)(F)F)(=O)=O)([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:37])[CH3:36].O>ClCCl>[CH2:1]([O:8][CH:9]1[CH2:14][CH2:13][CH:12]([O:15][CH2:16][CH:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[O:18][Si:35]([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:37])[CH3:36])[CH:11]([F:25])[CH2:10]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 69274788HCID 69274788, compound

Product 1

HCID 69274730HCID 69274730, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-{[4-(Benzyloxy)-2-fluorocyclohexyl]oxy}-1-phenylethanol (8.46 g, 24.6 mmol) in dichloromethane (100 mL) at 0° C. was added diisopropylethylamine (17.1 mL, 98.8 mmol) and TBSOTf (13.0 mL, 49.4 mmol). The reaction mixture was stirred for 5 min and then poured into water. The layers were separated and the aqueous extracted with dichloromethane (3×). The combined organic layers were washed with water and brine, dried over Na2SO4, filtered and concentrated. Purification by flash column chromatography (5% ethyl acetate in hexanes) gave (2-{[4-(Benzyloxy)-2-fluorocyclohexyl]oxy}-1-phenylethoxy)(tert-butyl)dimethylsilane (11.3 g, 100% yield) as a clear oil.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous extracted with dichloromethane (3×)
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by flash column chromatography (5% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-233e33d1bc574d17a3e03e16c728191f
Source dataset
uspto-grants-2008_11
Patent number
US07452893B2

Reaction notes

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