Triethylamine → Ethyl 3-(hexadecyloxy)-2-[(hexadecylthio)methyl]propanoate

HRID 1885448Notes

Reaction equation

HRID 1885448 reaction equation
[CH2:1]([O:17][CH2:18][C:19](=[CH2:25])[C:20]([O:22][CH2:23][CH3:24])=[O: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].C(N(CC)CC)C.[CH2:33]([SH:49])[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH3:48]>C(O)C>[CH2:1]([O:17][CH2:18][CH:19]([CH2:25][S:49][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH3:48])[C:20]([O:22][CH2:23][CH3:24])=[O: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

5

Reactant 3

HCID 8471TriethylamineHCID 18015HexadecanethiolHCID 12971817Ethyl 2-[(hexadecyloxy)methyl]-2-propenoate

Product 1

HCID 19764340Ethyl 3-(hexadecyloxy)-2-[(hexadecylthio)methyl]propanoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 20 g of 2-[(hexadecyloxy)methyl]-2-propenoic acid, ethyl ester and 10 ml of triethylamine in 60 ml of ethanol is added 53 ml of hexadecyl mercaptan. This mixture is stirred overnight, then the solvents removed and the residue purified by HPLC [hexane:ethyl acetate (9:1)], to give 32.9 g of the desired compound as a white waxy solid.

Workup

  1. customthe solvents removed
  2. customthe residue purified by HPLC [hexane:ethyl acetate (9:1)]

Sources & evidence

ORD record
ord-f22920ae98884709a68a514ecc876f5b
Source dataset
uspto-grants-1992_09
Patent number
US05144045

Reaction notes

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