Hexamethylphosphoramide → 2,3-Dihydroxypropyl 4-[14-(trimethylsilyl)tetradecylamino]benzoate

HRID 652023Notes

Reaction equation

HRID 652023 reaction equation
[CH3:1][Si:2]([CH3:28])([CH3:27])[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][CH2:16][NH:17][C:18]1[CH:26]=[CH:25][C:21]([C:22]([OH:24])=[O:23])=[CH:20][CH:19]=1.[OH-].[Na+].I[CH2:32][CH:33]([OH:36])[CH2:34][OH:35].CN(C)P(N(C)C)(N(C)C)=O>O.CCOCC>[CH3:28][Si:2]([CH3:1])([CH3:27])[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][CH2:16][NH:17][C:18]1[CH:19]=[CH:20][C:21]([C:22]([O:24][CH2:32][CH:33]([OH:36])[CH2:34][OH:35])=[O:23])=[CH:25][CH:26]=1

Participants

7

Reactant 4

HCID 12679HexamethylphosphoramideHCID 14798Sodium HydroxideHCID 921273-Iodo-1,2-propanediolHCID 138848624-[14-(Trimethylsilyl)tetradecylamino)benzoic acid

Product 1

HCID 201982882,3-Dihydroxypropyl 4-[14-(trimethylsilyl)tetradecylamino]benzoate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 7.17 g. of 4-[14-(trimethylsilyl)tetradecylamino]benzoic acid, 4.80 g. of 25% aqueous sodium hydroxide, and 12.6 g. of 3-iodo-1,2-propanediol in 50 ml. of hexamethylphosphoramide is stirred for 24 hours at ambient temperature, diluted with 100 ml. of ether and stirred for 5 days at ambient temperature. The mixture is treated with water and extracted with ether. The dried extracts are evaporated to yield the product as a white solid.

Workup

  1. additiondiluted with 100 ml
  2. extractionextracted with ether
  3. customThe dried extracts are evaporated

Sources & evidence

ORD record
ord-a6d2531bd5c5499092348ac7ad36608b
Source dataset
uspto-grants-1987_06
Patent number
US04670421

Reaction notes

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