2-[(12-Fluorododec-3-YN-1-YL)oxy]oxane → 12-fluoro-(Z)-3-dodecen-1-yl tetrahydropyranyl ether

HRID 1263081Notes

Reaction equation

HRID 1263081 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][CH2:9][C:10]#[C:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][F:20].[H][H]>CO.N1C2C(=CC=CC=2)C=CC=1.[Pd]>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[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]

Participants

6

Reactant 2

HCID 133725902-[(12-Fluorododec-3-YN-1-YL)oxy]oxaneHCID 178418361HCID 178418361, compound2×

Product 1

HCID 1337259212-fluoro-(Z)-3-dodecen-1-yl tetrahydropyranyl etherYield 99%

Reagents, catalysts & solvents 3

HCID 7047QuinolineCatalystHCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 12-fluoro-3-dodecyn-1-yl tetrahydropyranyl ether (0.5262 g, 1.85 mmol) (prepared as in Example 3 above) in methanol (10 mL) containing about 4 drops of quinoline is hydrogenated at room temperature over 5% palladium on barium sulfate (25 mg). The mixture is kept at about 762 psi of hydrogen until 41.5 ml (1.85 mmol) of hydrogen has been absorbed. The catalyst is then filtered off and the solvent removed in vacuo. The residue is purified by flash chromatography using hexane/ethyl acetate (9:1, v/v) to give 12-fluoro-(Z)-3-dodecen-1-yl tetrahydropyranyl ether (0.52 g, 99%) as a clear oil: Rf=0.65, hexane/ethyl acetate (7:3, v/v); IR (film) ν3025 (C=CH); and 1H-NMR δ1.20-1.80 (m, 18H), 2.05 (m,2H), 2.35 (br q, J=4 Hz, 2H), 3.60 (m, 4H), 4.41(dt, J=48 Hz, 2H), 4.56 (br s, 1H), 5.41 (m, 2H).

Workup

  1. customhas been absorbed
  2. filtrationThe catalyst is then filtered off
  3. customthe solvent removed in vacuo
  4. customThe residue is purified by flash chromatography

Sources & evidence

ORD record
ord-5a933fdceebf4c59823732e0f7ac84df
Source dataset
uspto-grants-1984_06
Patent number
US04455441

Reaction notes

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