Palmitoyl chloride → HCID 21279119, compound

HRID 2291613Notes

Reaction equation

HRID 2291613 reaction equation
[OH:1][CH2:2][C:3]1[S:11][C:10]2[C:9]3[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=3[O:7][CH:6]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:5]=2[CH:4]=1.[C:22](Cl)(=[O:38])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]>N1C=CC=CC=1>[C:22]([O:1][CH2:2][C:3]1[S:11][C:10]2[C:9]3[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=3[O:7][CH:6]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:5]=2[CH:4]=1)(=[O:38])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]

Participants

4

Reactant 2

HCID 8206Palmitoyl chlorideHCID 21279118HCID 21279118, compound

Product 1

HCID 21279119HCID 21279119, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A suspension of 5.9 g 4H-2-hydroxymethyl-4-phenyl-thieno[3,2-c][1]benzopyran and 5.8 g of palmitoyl chloride in 50 ml pyridine is stirred at room temperature for 4 h. After filtration, one adds 400 ml water to the filtrate. The precipitate which appears is collected. This material is dissolved in methylene chloride and this organic phase is washed with hydrochloric acid solution, then with water, dried and evaporated. The residue is purified by column chromatography on silicagel using a mixture of n-hexane and methylene chloride as eluant. Pure 4H-2-palmitoyloxymethyl-4-phenyl-thieno[3,2-c][1]benzopyran is obtained as a white powder; m.p. 64°-65° C.

Workup

  1. filtrationAfter filtration, one
  2. additionadds 400 ml water to the filtrate
  3. customThe precipitate which appears is collected
  4. dissolutionThis material is dissolved in methylene chloride
  5. washthis organic phase is washed with hydrochloric acid solution
  6. dry with materialwith water, dried
  7. customevaporated
  8. customThe residue is purified by column chromatography on silicagel
  9. additiona mixture of n-hexane and methylene chloride as eluant

Sources & evidence

ORD record
ord-7e8e0673822748a2962859ebfc11657e
Source dataset
uspto-grants-1989_01
Patent number
US04797414

Reaction notes

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