Boron trifluoride etherate → HCID 53649488, compound

HRID 1708490Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][CH:11]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]3[CH:30]=[CH:29][C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[N:22]=3)=[CH:15][CH:14]=2)O)=[CH:4][CH:3]=1.[C:31]([O:35][CH2:36][CH3:37])(=[O:34])[CH2:32][SH:33].B(F)(F)F.CCOCC>C(Cl)Cl>[CH2:36]([O:35][C:31](=[O:34])[CH2:32][S:33][CH:11]([C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]2[CH:30]=[CH:29][C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[N:22]=2)=[CH:15][CH:14]=1)[CH2:10][CH2:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)[CH3:37]

Participants

Conditions

Temperature: 0 °C

Procedure

To a mixture of 4-(4-chlorophenyl)-1 -[4-(2-quinolylmethoxy)phenyl]butan-1-ol from Example 2 (830 mg; 2 mmol) and ethyl thioglycolate (0.283 ml; 2.5 mmol) in methylene chloride (20 ml) at 0° C. was added boron trifluoride etherate (0.62 ml; 5 mmol) dropwise. The resulting mixture was stirred at 0° C. for 1 h and at room temperature for 1 h. After the mixture was concentrated in vacuo and the residue was purified by chromatography (silica gel; hexane-ethyl acetate 3:1) to afford 820 mg of {[4-(4-chlorophenyl)-1-(4-[2-quinolinylmethoxy]phenyl)butyl]thio}acetic acid ethyl ester.

Workup

concentrationAfter the mixture was concentrated in vacuo
customthe residue was purified by chromatography (silica gel; hexane-ethyl acetate 3:1)

Sources & evidence

ORD record: ord-b63a168632674f51b45ea6b36e6efbd6
Source dataset: uspto-grants-1994_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05358955

Reaction notes

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