Water → HCID 14771648, compound

HRID 1650623Notes

Reaction equation

HRID 1650623 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([O:24][CH2:25][CH:26]([CH2:28][O:29][C:30]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[OH:27])=[O:23])[CH:5]=[CH:6][CH:7]=1.N1C=CC=CC=1.[C:55](Cl)(=[O:57])[CH3:56].O>C(O)C>[I:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([O:24][CH2:25][CH:26]([CH2:28][O:29][C:30]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[O:27][C:55](=[O:57])[CH3:56])=[O:23])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 6367Acetyl chlorideHCID 14771647HCID 14771647, compound

Product 1

HCID 14771648HCID 14771648, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-[15-(m-Iodophenyl)pentadecanoyl]-3-O-trityl-rac-glycerol (0.34 g, 0.45 mmol) was dissolved in ethanol free CHCl3 (2.2 ml) in a two-necked flask. Pyridine (0.06 ml, 0.79 mmol) was added, followed by acetyl chloride (0.09 ml, 1.26 mmol). The reaction mixture was stirred for 7 hours, then H2O was added to destroy the excess acetyl chloride. This mixture was diluted with CHCl3, washed twice with 1 N HCl and once with brine. The organic layer was dried over MgSO4 and the solvent was evaporated. Chromatographic purification yielded pure compound 34, 1-[15-(m-iodophenyl)pentadecanoyl]-2-acetyl-3-O-trityl-rac-glycerol. (0.31 g, 86% yield).

Workup

  1. customto destroy the excess acetyl chloride
  2. additionThis mixture was diluted with CHCl3
  3. washwashed twice with 1 N HCl and once with brine
  4. dry with materialThe organic layer was dried over MgSO4
  5. customthe solvent was evaporated
  6. customChromatographic purification

Sources & evidence

ORD record
ord-490a51532a694caf8834934bb841180c
Source dataset
uspto-grants-1990_05
Patent number
US04925649

Reaction notes

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