HCID 10708156, compound → HCID 85977668, compound

HRID 1180335Notes

Reaction equation

HRID 1180335 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6](OS(C(F)(F)F)(=O)=O)=[CH:5][C:4]=1[O:17][CH3:18])=[O:2].[Si]([O:26][C:27]1[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][CH:28]=1)(C(C)(C)C)(C)C>>[OH:26][C:27]1[CH:32]=[CH:31][C:30]([C:6]2[CH:7]=[CH:8][C:3]([CH:1]=[O:2])=[C:4]([O:17][CH3:18])[CH:5]=2)=[CH:29][CH:28]=1

Participants

3

Reactant 2

HCID 10708156HCID 10708156, compoundHCID 111078154-(tert-Butyldimethylsilyloxy)phenylboronic Acid (contains varying amounts of Anhydride)

Product 1

HCID 85977668HCID 85977668, compound

Procedure

The title compound was prepared by reacting trifluoro-methanesulfonic acid 4-formyl-3-methoxy-phenyl ester (11.0 mmol) with 4-tert-butyl-dimethylsilyoxyphenyl-boronic acid (3.50 g, 13.86 mmol) according to Method B to yield 880 mg (35%, over two steps) of yellowish solid: mp 159-161° C.; 1H NMR (DMDO-d6): δ 4.01 (3H, s), 6.89 (2H, d, J=8.62 Hz), 7.31 (1H, d, J=8.16 Hz), 7.36 (1H, d, J=1.15 Hz), 7.66 (2H, d, J=8.63 Hz), 7.72 (1H, d, J=8.09 Hz), 9.80 (1H, s), 10.34 (1H, s); mp 159-161° C.; IR 1660 cm−1; MS (ESI) m/z 227 (M−H)−, 229 (M+H)+.

Workup

  1. customto yield 880 mg (35%, over two steps) of yellowish solid

Sources & evidence

ORD record
ord-93d2bc9f8c4542ea81f908297e501bb1
Source dataset
uspto-grants-2007_10
Patent number
US07279600B2

Reaction notes

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