Veratroyl chloride → HCID 21182672, compound

HRID 1387035Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[C:6](Cl)=[O:7].[CH2:14]([O:21][C:22]1[CH:23]=[CH:24][C:25]2[CH:29]=[C:28]([N:30]([CH3:32])[CH3:31])[S:27][C:26]=2[CH:33]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>ClC1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:6]([C:29]2[C:25]3[CH:24]=[CH:23][C:22]([O:21][CH2:14][C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)=[CH:33][C:26]=3[S:27][C:28]=2[N:30]([CH3:32])[CH3:31])=[O:7])[CH:9]=[CH:10][C:11]=1[O:12][CH3:13]

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of 3,4-dimethoxybenzoyl chloride (1.250 g, 6.231 mmol) in 18 miL of chlorobenzene was added 6-benzyloxy-2-(dimethylamino)benzo[b]thiophene (Part B) (1.059 g, 3.738 mmol). The dark blue reaction mixture was then heated to 110° C. and stirred for 17 h by which time the solution turned to brown. The brown solution was then quenched at 0° C. with 30 mL of saturated aqueous NaHCO3 solution and extracted with EtOAc (2×200 mL). The combined organic layers were washed with 200 mL with brine, dried over MgSO4, concentrated under reduced pressure, and purified by flash chromatography (silica gel, 50:50 EtOAc-hexanes) to afford 1.265 g (2.826 mmol, 76%) of a yellow foam.

Workup

customThe dark blue reaction mixture
customThe brown solution was then quenched at 0° C. with 30 mL of saturated aqueous NaHCO3 solution
extractionextracted with EtOAc (2×200 mL)
washThe combined organic layers were washed with 200 mL with brine
dry with materialdried over MgSO4
concentrationconcentrated under reduced pressure
custompurified by flash chromatography (silica gel, 50:50 EtOAc-hexanes)

Sources & evidence

ORD record: ord-20c393805c7d42b3a7f7912732771bba
Source dataset: uspto-grants-2001_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06265575B1

Reaction notes

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