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

HRID 34303Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 34303
[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]

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-141bed5bb15d477392e985523236fcd2
Quelldatensatz
uspto-grants-1988_08
Patentnummer
US04761404

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