Hexane → HCID 15917440, compound

HRID 648096Notes

Reaction equation

HRID 648096 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][C:5]2[CH2:6][C:7]3([O:18][C:4]=2[CH:3]=1)[C:16]1[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=1)[CH2:10][N:9](C)[CH2:8]3.Cl[C:22]([O:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:23].CCCCCC>ClCCl>[Cl:1][C:2]1[CH:20]=[CH:19][C:5]2[CH2:6][C:7]3([O:18][C:4]=2[CH:3]=1)[C:16]1[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=1)[CH2:10][N:9]([C:22]([O:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:23])[CH2:8]3

Participants

5

Reactant 3

HCID 8058HexaneHCID 15891Phenyl chloroformateHCID 15917438HCID 15917438, compound

Product 1

HCID 15917440HCID 15917440, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To an ice cold solution of 6-chloro-2'-methylspiro[benzofuran-2(3H),4'(2'H)-isoquinoline] (5.0 g) in dichloromethane (150 ml) is slowly added dropwise phenyl chloroformate (3.7 g) in dichloromethane (20 ml). The mixture is stirred at ambient temperature overnight. Removal of the solvent in vacuo yields an orange oil which solidifies upon trituration with hexane. An analytical sample is twice recrystallized from hexane to yield product as a solid (6.6 g, 99%), mp 138°-140°.

Workup

  1. customRemoval of the solvent in vacuo
  2. customyields an orange oil which
  3. customAn analytical sample is twice recrystallized from hexane

Sources & evidence

ORD record
ord-076e426143af4439a000c173bacff03b
Source dataset
uspto-grants-1983_10
Patent number
US04410699

Reaction notes

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