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

HRID 34303노트

반응식

HRID 34303 반응식
[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]

참가 물질

4

반응물 2

HCID 212991511-Hexadecyloxy-2-fluoromethyl-3-triphenylmethoxypropanHCID 21893785Acetic Acid Mixture with Hydrobromic Acid

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-141bed5bb15d477392e985523236fcd2
출처 데이터셋
uspto-grants-1988_08
특허 번호
US04761404

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