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Carbon Tetrachloride → 7-Chloromethyl-4-(3-thienyl)coumarin

HRID 21575
Notes
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Reaction equation

HRID 21575 reaction equation
O[CH2:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([C:14]3[CH:18]=[CH:17][S:16][CH:15]=3)=[CH:8][C:9](=[O:13])[O:10]2)=[CH:5][CH:4]=1.CN(C)P(N(C)C)N(C)C.C(Cl)(Cl)(Cl)[Cl:30]>C1COCC1.CCOCC>[Cl:30][CH2:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([C:14]3[CH:18]=[CH:17][S:16][CH:15]=3)=[CH:8][C:9](=[O:13])[O:10]2)=[CH:5][CH:4]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 5943Carbon TetrachlorideHCID 15355Hexamethylphosphorous triamideHCID 157805587-Hydroxymethyl-4-(3-thienyl)coumarin

Product 1

HCID 157805597-Chloromethyl-4-(3-thienyl)coumarin

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028
On this pageParticipantsProcedureWorkupSources & evidenceReaction notes
Tetrahydrofuran
Solvent

Procedure

To a solution of the alcohol from Step 1 (1.65 g) and hexamethylphosphorous triamide in 35 mL THF at 0° C. was added CCl4 (1.3 mL) and the mixture stirred for 30 min. The mixture was diluted with Et2O, filtered, concentrated and the residue chromatographed (30% EtOAc/hexane) to provide the title compound as a solid, m.p. 125°-127° C.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. customthe residue chromatographed (30% EtOAc/hexane)

Sources & evidence

ORD record
ord-41bf4b14ae7e4194a8b652aa27b29dc4
Source dataset
uspto-grants-1995_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05424320

Reaction notes

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