HCID 70506352, compound → HCID 86739508, compound

HRID 1263085Notes

Reaction equation

HRID 1263085 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][CH2:20][CH2:21][F:22]>CO>[F:22][CH2:21][CH2:20][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

HCID 70506352HCID 70506352, compound

Product 1

HCID 86739508HCID 86739508, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Following the procedure described in Example 6 using 353.6 mg (1.26 mmol) of 14-fluoro-(Z)-3-tetradecen-1-yl tetrahydropyranyl ether and 350 mg Dowex in about 10 ml of methanol affords 14-fluoro-(Z)-3-tetradecen-1-ol. Purification by flash chromatography affords 14-fluoro-(Z)-3-tetradecen-1-ol (211.8 mg, 73%) as a clear colorless oil: Rf=0.27, hexane/ethyl acetate (7:3, v/v); IR (film) ν3200-3500 (OH), 3025 (alkane CH); and 1H-NMR (CDCl3) δ1.20-1.70 (m, 16H), 2.10 (m, 2H), 2.39 (br q, J=5 Hz, 2H), 3.65 (t, J=6 Hz, 2H), 4.41 (dt, J=48 Hz, 6 Hz, 2H), 5.45 (m, 2H).

Sources & evidence

ORD record
ord-59e8068bcd694d71a787f8006f27cbda
Source dataset
uspto-grants-1984_06
Patent number
US04455441

Reaction notes

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