12-fluoro-(Z)-3-dodecen-1-yl tetrahydropyranyl ether → 12-fluoro-(Z)-3-dodecen-1-ol
Reaction equation
O1CCCCC1[O:7][CH2:8][CH2:9]/[CH:10]=[CH:11]\[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][F:20]>CO>[F:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]/[CH:11]=[CH:10]\[CH2:9][CH2:8][OH:7]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 45 °C
Procedure
To a solution of 12-fluoro-(Z)-3-dodecen-1-yl tetrahydropyranyl ether (0.5242 g, 1.83 mmol) (prepared as in Example 5 above) in methanol (10 ml) is added Dowex resin (0.5 g) and the mixture is heated at 45° C. overnight (Bongini et. al., Synthesis, 618, 1979). The resin is then filtered off and the solvent is removed in vacuo. The crude product is purified by flash chromatography using hexane/ethyl acetate (93:7, v/v) to give 12-fluoro-(Z)-3-dodecen-1-ol (312 mg, 83%) as a clear colorless oil: Rf=0.36, hexane/ethyl acetate (7:3, v/v); IR (film ν3100-3550 (OH), 3000 (C=CH); and H NMR (CDCl3) δ1.25-1.75 (m, 12H), 2.15 (m, 2H), 2.35 (br q, J=6 Hz, 2H), 3.65 (t, J=9 Hz, 2H), 4.41(dt, J=48 Hz, 6 Hz, 2H), 5.46 (m, 2H).
Workup
- custom(Bongini et. al., Synthesis, 618, 1979)
- filtrationThe resin is then filtered off
- customthe solvent is removed in vacuo
- customThe crude product is purified by flash chromatography
Sources & evidence
- ORD record
- ord-c5d003f873724ca6b7f3080bf1e4a7bc
- Source dataset
- uspto-grants-1984_06
- Patent number
- US04455441
Reaction notes
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