Dichloromethane → HCID 20521687, compound

HRID 223632Notes

Reaction equation

HRID 223632 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][C:5](=[O:26])[CH2:6][PH:7]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(Cl)[Cl:28]>>[Cl-:28].[OH:1][CH2:2][CH2:3][CH2:4][C:5](=[O:26])[CH2:6][P+:7]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

3

Reactant 2

HCID 6344DichloromethaneHCID 178520687HCID 178520687, compound

Product 1

HCID 20521687HCID 20521687, compound

Conditions

Temperature
50 °C

Procedure

2.3 g of (5-hydroxy-2-oxopentyl)triphenylphosphorane was dissolved in methylene chloride and extracted 4 times with aqueous hydrochloric acid (pH 1 to 2) and the extracts were combined, sodium chloride added and then extracted with methylene chloride (4×50 ml). The organic extracts were combined, dried over sodium sulfate, and the solvent removed under nitrogen gas followed by heating to 50° C./0.5 mm Hg for 6 hours and crystallization from acetone to give 1.9 g of product, m.p. 143°-145° C. identical with that obtained by the process in Example 10.

Workup

  1. extractionextracted 4 times with aqueous hydrochloric acid (pH 1 to 2)
  2. additionsodium chloride added
  3. extractionextracted with methylene chloride (4×50 ml)
  4. dry with materialdried over sodium sulfate
  5. customthe solvent removed under nitrogen gas
  6. customcrystallization from acetone

Sources & evidence

ORD record
ord-c2bbcff5d9904590acd278752efd1175
Source dataset
uspto-grants-1982_10
Patent number
US04355182

Reaction notes

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