1-Hexadecyloxy-2-fluoromethyl-3-triphenylmethoxypropan → 3-Hexadecyloxy-2-fluoromethyl-1-propanol

HRID 34303Notes

Reaction equation

HRID 34303 reaction equation
[CH2:1]([O:17][CH2:18][CH:19]([CH2:41][F:42])[CH2:20][O:21]C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=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].Br.C(O)(=O)C>C(O)(=O)C>[CH2:1]([O:17][CH2:18][CH:19]([CH2:41][F:42])[CH2:20][OH:21])[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 212991511-Hexadecyloxy-2-fluoromethyl-3-triphenylmethoxypropanHCID 21893785Acetic Acid Mixture with Hydrobromic Acid

Product 1

HCID 212991423-Hexadecyloxy-2-fluoromethyl-1-propanolYield 88%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 0.750 g (123 mmol) of 10 in 5 ml glacial acetic acid was cooled to 0°. To this was added 2 ml of HBr-acetic acid and the mixture was stirred at 0° for 45 seconds. The solution was filtered and the filtrate was poured into ice water and the mixture was partitioned between methylene chloride and water. The aqueous layer was washed with two portions of methylene chloride and the organic extracts were washed with aqueous Na2CO3 and water, dried over Na2SO4, and concentrated. The residue was chromatographed on silica gel using hexane-ethyl acetate eluent (9:1, v/v) to afford 0.388 g (88%) of the title compound (11) as a colorless wax, m.p. 34°. NMR (CDCl3, (CH3)4Si); δ0.90 (t, 3H, J=6 Hz), 1.25 (s, br, 26H), 1.59 (m, 2H), 2.10 (s, br, --OH), 2.19 (d of septets, 1H, JH--H)=6 Hz, JH--F =21 Hz), 3.45 (t, 2H, J=6.5 Hz), 3.63 (d, 2H, J=6 Hz), 3.85 (d, 2H, J=6 Hz, CH2OH), 4.64 (d of d, 2H, JH--H =6 Hz, JH-F=47 Hz).

Workup

  1. filtrationThe solution was filtered
  2. additionthe filtrate was poured into ice water
  3. customthe mixture was partitioned between methylene chloride and water
  4. washThe aqueous layer was washed with two portions of methylene chloride
  5. washthe organic extracts were washed with aqueous Na2CO3 and water
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-141bed5bb15d477392e985523236fcd2
Source dataset
uspto-grants-1988_08
Patent number
US04761404

Reaction notes

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