Acetic Acid → 6-[2-(Tert-butyl-dimethyl-silanyloxy)-ethoxy]-3-chloro-2-fluoro-benzaldehyde

HRID 1728073Notes

Reaction equation

HRID 1728073 reaction equation
[C:1]([Si:5]([O:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([F:19])[CH:13]=1)([CH3:7])[CH3:6])([CH3:4])([CH3:3])[CH3:2].C(NC(C)C)(C)C.[Li].CN(C)[CH:30]=[O:31].C(O)(=O)C>O1CCCC1>[C:1]([Si:5]([CH3:7])([CH3:6])[O:8][CH2:9][CH2:10][O:11][C:12]1[C:13]([CH:30]=[O:31])=[C:14]([F:19])[C:15]([Cl:18])=[CH:16][CH:17]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6228DimethylformamideHCID 45051747Lithium diisopropylamineHCID 57566201Tert-butyl-[2-(4-chloro-3-fluoro-phenoxy)-ethoxy]-dimethyl-silane

Product 1

HCID 575658686-[2-(Tert-butyl-dimethyl-silanyloxy)-ethoxy]-3-chloro-2-fluoro-benzaldehydeYield 41%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a manner similar to the method described in example 52a, tert-butyl-[2-(4-chloro-3-fluoro-phenoxy)-ethoxy]-dimethyl-silane (14.3 g, 47 mmol) prepared in example 132a was reacted with lithium diisopropylamine (34 mL, 1.8 M in THF, 61 mmol), N,N-dimethyl-formamide (4.7 mL, 61 mmol) and quenched with acetic acid (14 g, 234 mmol) in tetrahydrofuran to give 6-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-3-chloro-2-fluoro-benzaldehyde as a white solid (Yield: 6.4 g, 41%).

Sources & evidence

ORD record
ord-0b92d965735e4200a3f397f54586d855
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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