1,2-Dimethoxyethane → HCID 86737116, compound

HRID 2058325Notes

Reaction equation

HRID 2058325 reaction equation
[CH2:1]([OH:14])[CH2:2][CH2:3][CH2:4][C:5]#[C:6][C:7]#[C:8][CH2:9][CH2:10][CH2:11][CH2:12][OH:13].C[O:16][CH2:17][CH2:18]OC.C(N(CC)CC)C.[CH2:28]([N:46]=[C:47]=[O:48])[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][CH2:42][CH2:43][CH2:44][CH3:45]>CCCCCCC>[CH2:28]([NH:46][C:47]([O:13][CH2:12][CH3:11])=[O:48])[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][CH2:42][CH2:43][CH2:44][CH3:45].[CH2:28]([NH:46][C:47]([O:16][CH2:17][CH3:18])=[O:48])[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][CH2:42][CH2:43][CH2:44][CH3:45].[CH2:12]([OH:13])[CH2:11][CH2:10][CH2:9][C:8]#[C:7][C:6]#[C:5][CH2:4][CH2:3][CH2:2][CH2:1][OH:14]

Participants

6

Reactant 4

HCID 80711,2-Dimethoxyethane3×HCID 8471TriethylamineHCID 66988Octadecyl isocyanateHCID 5608785,7-Dodecadiyne-1,12-diol

Product 1

HCID 86737116HCID 86737116, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Procedure

A mixture of 40 parts 5,7-dodecadiyne-1,12-diol, 215 parts 1,2-dimethoxyethane, 1 part dibutyltin-di-2-ethylhexanoate and 15 parts triethylamine was prepared and the resulting mixture was stirred vigorously. A solution of 133 parts n-octadecylisocyanate in 44 parts of 1,2-dimethoxyethane was added dropwise over a period of 60 min. The reaction temperature rose to 42° C. from 18° C. within 50 min. and then subsided. After the addition, 80 parts of 1,2-dimethoxyethane was then added to the reaction mixture and the mixture was stirred for an additional 2 hrs. To this mixture was added 1390 parts of heptane. The precipitate was collected by filtration, washed with petroleum ether (bp 30°-60° C.) and dried, giving 154.6 parts (99% yield) of desired product, mp 118°-119° C.

Workup

  1. customwas prepared
  2. additionwas then added to the reaction mixture
  3. stirringthe mixture was stirred for an additional 2 hrs
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with petroleum ether (bp 30°-60° C.)
  6. customdried

Sources & evidence

ORD record
ord-793c8dfe5ccd4892abd4ec5e71d3aa03
Source dataset
uspto-grants-1980_07
Patent number
US04215208

Reaction notes

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