Lithium Bromide → (+/-)-1-Hexadecylthio-2-ethoxy-3-bromopropane

HRID 977287Notes

Reaction equation

HRID 977287 reaction equation
[CH2:1]([S:17][CH2:18][CH:19]([O:22][CH3:23])[CH2:20][Br:21])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[CH2:24](SCC(COS(C)(=O)=O)OCC)CCCCCCCCCCCCCCC.[Br-].[Li+]>>[CH2:1]([S:17][CH2:18][CH:19]([O:22][CH2:23][CH3:24])[CH2:20][Br:21])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

4

Reactant 3

HCID 82050Lithium BromideHCID 14522779(+/-)-1-S-hexadecyl-2-O-ethyl-3-O-mesylthioglycerolHCID 14522781(+)-1-Hexadecylthio-2-methoxy-3-bromopropane

Product 1

HCID 14522782(+/-)-1-Hexadecylthio-2-ethoxy-3-bromopropaneYield 93%

Procedure

This compound was prepared in an analogous manner to that (±)-1-hexadecylthio-2-methoxy-3-bromopropane with 6.0 grams (0.014 mole) of (±)-1-S-hexadecyl-2-O-ethyl-3-O-mesylthioglycerol and 20.0 grams (0.07 mole) of lithium bromide. Silica gel column chromatography as before gave 5.5 grams (93%) of product as an oil. 1H-NMR (CDCl3): delta, 0.87(t, 3H, terminal methyl), 1.2-1.6[m, 31H, (CH2)14, CH3 --CH2 --O], 2.58(m, 2H, S--CH2), 2.62(m, 2H, CH--CH2 --S), 3.3-3.5(m, 5H, CH, CH3 --CH2 --O, CH2 --Br).

Sources & evidence

ORD record
ord-11bdd9ac3f4740a9955dacc01802f5cb
Source dataset
uspto-grants-1997_03
Patent number
US05614548

Reaction notes

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