Tetrabutylammonium Fluoride → 1-Hexadecyloxy-2-fluoromethyl-3-triphenylmethoxypropan

HRID 34302Notes

Reaction equation

HRID 34302 reaction equation
[CH2:1]([O:17][CH2:18][CH:19]([CH2:41]OS(C)(=O)=O)[CH2:20][O:21][C:22]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[F-:47].C([N+](CCCC)(CCCC)CCCC)CCC>CN(C)C=O>[CH2:1]([O:17][CH2:18][CH:19]([CH2:41][F:47])[CH2:20][O:21][C:22]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 212991491-Hexadecyloxy-2-methanesulfonyloxymethyl-3-triphenylmethoxypropane

Product 1

HCID 212991511-Hexadecyloxy-2-fluoromethyl-3-triphenylmethoxypropanYield 89.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 9 (1.10 g, 1.70 mmol) and tetrabutylammonium fluoride (2.00 g, 7.60 mmol) in dry N,N-dimethylformamide was stirred under N2 at 60°. After 18 hours, the solution was concentrated and the residue was partitioned between hexane and water. The hexane layer was washed 3 times with water, dried over Na2SO4 and concentrated. Chromatography on silica gel using hexane-CH2Cl2 (1:1, v/v) afforded 0.871 g (87%) of the title compound (10) as a colorless wax, m.p. 32°. NMR (CDCl3, --(CH3)4Si); δ0.90 (t, 3H, J=6 Hz, --CH3), 1.25 (s, 26H, --CH2 --), 1.55 (m, 2H, --OCH2CH2R), 2.32 (d of septets, 1H, JH--H =6 Hz, JH--F =23.5 Hz, --CH), 3.19 (d, 2H, J=6.0 Hz, --CH2OTr), 3.36 (t, 2H, J=6.5 Hz, --OCH2R), 3.49 (d, 2H, J=6.0 Hz, --CH2OR), 4.59 (d of d, 2H, JHH =6.0 Hz, JH--F =47.5 Hz, --CH2F), 7.2-7.52 (m, 15H, --C(C6H5)3)

Workup

  1. concentrationthe solution was concentrated
  2. customthe residue was partitioned between hexane and water
  3. washThe hexane layer was washed 3 times with water
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-bfce0d150a59483c9cd98e733c3c7983
Source dataset
uspto-grants-1988_08
Patent number
US04761404

Reaction notes

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