Dimethylformamide → 5-(Tert-butyl-dimethyl-silanyloxy)-3-(tert-butyl-diphenyl-silanyloxy)-2-fluoro-benzaldehyde

HRID 1266712Notes

Reaction equation

[C:1]([Si:5]([CH3:33])([CH3:32])[O:6][C:7]1[CH:12]=[CH:11][C:10]([F:13])=[C:9]([O:14][Si:15]([C:28]([CH3:31])([CH3:30])[CH3:29])([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:8]=1)([CH3:4])([CH3:3])[CH3:2].C([Li])(CC)C.CN([CH:42]=[O:43])C>C1COCC1.C1CCCCC1>[C:1]([Si:5]([CH3:33])([CH3:32])[O:6][C:7]1[CH:8]=[C:9]([O:14][Si:15]([C:28]([CH3:31])([CH3:30])[CH3:29])([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:10]([F:13])=[C:11]([CH:12]=1)[CH:42]=[O:43])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of 55.0 g of 4-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-diphenyl-silanyloxy)-fluorobenzene described in example 3.1 in 120 ml THF was cooled to −78° C. Within 30 min 97 ml of an 1.3 M solution of sec-butyllithium in cyclohexane was added dropwise. After stirring at −78° C. for an hour, 9.7 DMF in 18.3 ml THF was added within 20 min. The mixture was stirred at −78° C. for 1 hr, then warmed to r.t. within 90 min and quenched with 300 ml ice-cold water. The product was isolated by extraction with Et2O to yield 60.6 g 5-(tert-butyl-dimethyl-silanyloxy)-3-(tert-butyl-diphenyl-silanyloxy)-2-fluoro-benzaldehyde as yellow liquid.

Workup

stirringThe mixture was stirred at −78° C. for 1 hr
temperaturewarmed to r.t. within 90 min
customquenched with 300 ml ice-cold water
customThe product was isolated by extraction with Et2O

Sources & evidence

ORD record: ord-d0d957ef31914c3ea395eab8e348d2bb
Source dataset: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06548694B2

Reaction notes

Loading…