Dimethylformamide → 3-[6-(Triphenylmethoxy)hexyloxy]-2-methylenepropan-1-ol

HRID 2166440Notes

Reaction equation

[H-].[Na+].CN(C)[CH:5]=[O:6].Cl[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][O:15][C:16]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>O>[C:17]1([C:16]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[O:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][O:15][CH2:14][C:13](=[CH2:12])[CH2:5][OH:6])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

Conditions

Temperature: 85 °C

Procedure

Sodium hydride (from 55-60% oil dispersion (0.52 g) washed with pentane (3×3 ml)), dry dimethylformamide (20 ml), and 2-metyylenepropane-1,3-diol (1.0 g) were mixed. After 1 hour when H2 -evolution had ceased 1-chloro-6-(triphenylmethoxy)hexane (4.2 g) was added, and the mixture was stirred for 3 hours at 85° C. After cooling water (20 ml) was carefully added, and the mixture was extracted with ether (2×100 ml). The ether extracts were washed with water (100 ml), dried over magnesium sulfate and evaporated to dryness in vacuo. The product was purified through a column of silica gel 60 (70-230 mesh, 40 g) eluting with ether. Futher purification was achieved by chromatography on Waters PrepLC®/System 500A using a prepPAK®-500/SILICA cartridge with ether/pentane 1:2 followed by ether/pentane 1:1 as eluent.

Workup

additionwas carefully added
extractionthe mixture was extracted with ether (2×100 ml)
washThe ether extracts were washed with water (100 ml)
dry with materialdried over magnesium sulfate
customevaporated to dryness in vacuo
customThe product was purified through a column of silica gel 60 (70-230 mesh, 40 g)
washeluting with ether
customFuther purification

Sources & evidence

ORD record: ord-0d383f45eb3c47559b2a5d2a8c8d6fa7
Source dataset: uspto-grants-1990_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04945098

Reaction notes

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