Boron Trichloride → Raloxifene Bismethyl Ether (hydrochloride)

HRID 2784

Reaction equation

HRID 2784 reaction equation
B(Cl)(Cl)[Cl:2].[CH3:5][O:6][C:7]1[CH:8]=[CH:9][C:10]2[C:14]([C:15](=[O:31])[C:16]3[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][N:25]4[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]4)=[CH:18][CH:17]=3)=[C:13]([C:32]3[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=3)[S:12][C:11]=2[CH:40]=1>C(Cl)Cl>[ClH:2].[CH3:5][O:6][C:7]1[CH:8]=[CH:9][C:10]2[C:14]([C:15](=[O:31])[C:16]3[CH:17]=[CH:18][C:19]([O:22][CH2:23][CH2:24][N:25]4[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]4)=[CH:20][CH:21]=3)=[C:13]([C:32]3[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=3)[S:12][C:11]=2[CH:40]=1

Participants

4

Reactant 2

HCID 25135Boron TrichlorideHCID 10767755Raloxifene Bismethyl Ether

Product 1

HCID 45260096Raloxifene Bismethyl Ether (hydrochloride)

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of the compound prepared as described in Preparation 1 (8.46 grams) and the acid chloride prepared as described in Preparation 4 (10.0 grams) in methylene chloride (350 mL) was cooled to about 20°-25° C. The cool mixture was treated with boron trichloride (2.6 mL), and the resulting mixture mechanically stirred. The reaction was monitored by HPLC using the assay described above. After 85 minutes, the in situ HPLC yield based on a 6-methoxy-2-(4-methoxyphenyl)-3-[4-(2-piperidinoethoxy)benzoyl]benzo[b]thiophene standard was 88%.

Workup

  1. additionA mixture of the compound
  2. customprepared
  3. temperaturewas cooled to about 20°-25° C
  4. customthe in situ HPLC yield

Sources & evidence

ORD record
ord-8147e79bd48043f3aa5c475b74c99072
Source dataset
uspto-grants-1998_03
Patent number
US05731327

Linked notes

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