Boron Trichloride → HCID 19736745, compound

HRID 326303Notes

Reaction equation

HRID 326303 reaction equation
[Cl:1][C:2]1[C:16]2[O:15][C:9]3([CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]3)[CH2:8][C:7](=[O:17])[C:6]=2[C:5]([O:18]C)=[CH:4][C:3]=1[O:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23].B(Cl)(Cl)Cl>ClCCl>[Cl:1][C:2]1[C:16]2[O:15][C:9]3([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]3)[CH2:8][C:7](=[O:17])[C:6]=2[C:5]([OH:18])=[CH:4][C:3]=1[O:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23]

Participants

4

Reactant 2

HCID 25135Boron TrichlorideHCID 19736701HCID 19736701, compound

Product 1

HCID 19736745HCID 19736745, compoundYield 77.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Ethyl 2-{(8-chloro-5-methoxy-3,4-dihydro-4-oxospiro[2H-1-benzopyran-2,1'-cyclohexan ]-7-yl)oxy}acetate (65-3, prepared in Preparation 65) (0.575 g, 1.50 mmol) is dissolved in dry dichloromethane (3 ml). To the solution is added dropwise a 2M boron trichloride solution in dichloromethane (1.5 ml, 3.0 mmol) at -75° to -70° C. After stirring at -70° to -50° C. for 1.5 hours, ice-cold water is added thereto and the mixture is extracted with dichloromethane. Organic layer is separated, washed with aqueous sodium bicarbonate, dried, and concentrated. The residue is applied to a silica gel column and eluted with a mixture of acetonitrile and dichloromethane (1:9) to yield the title compound as a crystalline solid (0.428 g, yield 77.4%). Recrystallization from diethyl ether gives a product having a melting point of 110°-111° C.

Workup

  1. additionice-cold water is added
  2. extractionthe mixture is extracted with dichloromethane
  3. customOrganic layer is separated
  4. washwashed with aqueous sodium bicarbonate
  5. customdried
  6. concentrationconcentrated
  7. washeluted with a mixture of acetonitrile and dichloromethane (1:9)

Sources & evidence

ORD record
ord-4d47a23a92634d5c89e517d4142a9832
Source dataset
uspto-grants-1993_12
Patent number
US05268386

Reaction notes

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