Dichloroacetic Acid → HCID 22633848, compound

HRID 1369314Notes

Reaction equation

HRID 1369314 reaction equation
ClC(Cl)C(O)=O.COC1C=CC(C([O:28][CH2:29][CH2:30][O:31][CH2:32][CH2:33][O:34][CH2:35][CH2:36][O:37][CH2:38][CH2:39][O:40][N:41]2[C:45](=[O:46])[C:44]3=[CH:47][CH:48]=[CH:49][CH:50]=[C:43]3[C:42]2=[O:51])(C2C=CC=CC=2)C2C=CC(OC)=CC=2)=CC=1>CO>[C:42]1(=[O:51])[N:41]([O:40][CH2:39][CH2:38][O:37][CH2:36][CH2:35][O:34][CH2:33][CH2:32][O:31][CH2:30][CH2:29][OH:28])[C:45](=[O:46])[C:44]2=[CH:47][CH:48]=[CH:49][CH:50]=[C:43]12

Participants

4

Reactant 2

HCID 6597Dichloroacetic AcidHCID 22633854HCID 22633854, compound

Product 1

HCID 22633848HCID 22633848, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of dichloroacetic acid in CH2C32 (100 mL, 3:97, v/v) and methanol (20 mL) was added to N-[11-(4,4′-dimethoxytrityloxy)-3,6,9-trioxaundecanyloxy]phthalimide (2.3 g, 3.6 mmol), and the reaction mixture was stirred for 18 hours. All volatile material was evaporated in vacuo and the residue was dissolved in CH2Cl2 (10 mL). Silica gel column purification using an eluent system with a stepwise gradient of acetic acid in CH2Cl2 (0-4%) gave 0.88 g (72%) of 11-(phthalimidooxy)-3,6,9-trioxaundecan-1-ol after coevaporation of the pooled fractions with water and pyridine.

Workup

  1. customAll volatile material was evaporated in vacuo
  2. dissolutionthe residue was dissolved in CH2Cl2 (10 mL)
  3. customSilica gel column purification

Sources & evidence

ORD record
ord-e8866eb9969b48148081e784a1c1f53f
Source dataset
uspto-grants-2003_06
Patent number
US06576752B1

Reaction notes

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