1-Bromohexadecane → 2-[(Hexadecyloxy)methyl]-4-heneicosyn-1-ol

HRID 248152Notes

Reaction equation

[CH2:1]([CH:20]([CH2:23][OH:24])[CH2:21][OH:22])[C:2]#[C:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].[H-].[Na+].[CH2:27](Br)[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42]>CN(C)C=O>[CH2:42]([O:24][CH2:23][CH:20]([CH2:1][C:2]#[C:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:21][OH:22])[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH3:27]

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 5.0 g of 2-(2-nonadecynyl)-1,3-propanediol, 75 ml of N,N-dimethylformamide, 710 mg of 60% sodium hydride and 5.4 ml of hexadecyl bromide is heated at 70° C. for 2 hours and then evaporated. The residue is purified by flash chromatography with an ethyl acetate:petroleum ether gradient to give 5.8 g of the desired compound as white crystals, mp. 46°-47° C.

Workup

customevaporated
customThe residue is purified by flash chromatography with an ethyl acetate

Sources & evidence

ORD record: ord-e84628cc3019426fa7d03f5b682bc102
Source dataset: uspto-grants-1993_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05208223

Reaction notes

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