2-[(6-bromohexyl)oxy]tetrahydro-2H-pyran → 1-(6-Tetrahydropyranyloxyhexyl)-1-hydroxymethylcyclopent-3-ene

HRID 372177Notes

Reaction equation

HRID 372177 reaction equation
[CH:1]1([C:6]([O:8]C)=O)[CH2:5][CH:4]=[CH:3][CH2:2]1.[O:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]1[O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]Br>>[O:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]1[O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:1]1([CH2:6][OH:8])[CH2:2][CH:3]=[CH:4][CH2:5]1

Participants

3

Reactant 2

HCID 1038602-[(6-bromohexyl)oxy]tetrahydro-2H-pyranHCID 1514118Methyl cyclopent-3-ene-1-carboxylate

Product 1

HCID 540215301-(6-Tetrahydropyranyloxyhexyl)-1-hydroxymethylcyclopent-3-ene

Procedure

The above procedure was repeated except that methyl cyclopent-3-ene carboxylate (prepared as described by A. H. Schmid and A. W. Wolkoff, J. Org. Chem. 32, 254 (1967)) was used with the 6-tetrahydropyranyloxyhexyl bromide of part D of this example and 1-(6-tetrahydropyranyloxyhexyl)-1-hydroxymethylcyclopent-3-ene was obtained as an oil (IR 3400, 3010 cm-1, nmr τ 4.4, 5.4, 6.35, 7.8, 8.5).

Workup

  1. customprepared

Sources & evidence

ORD record
ord-59ea908c77094c7bb537fe79ec29bf7c
Source dataset
uspto-grants-1978_05
Patent number
US04089897

Reaction notes

Loading…