Glycolic Acid → (Vinyl-2-ylidenetris(oxy))tris(trimethylsilane)

HRID 1155210Notes

Reaction equation

HRID 1155210 reaction equation
[C:1]([OH:5])(=[O:4])[CH2:2][OH:3].[CH3:6][Si:7](Cl)([CH3:9])[CH3:8]>O1CCCC1>[CH3:6][Si:7]([CH3:9])([CH3:8])[O:4][C:1]([O:5][Si:7]([CH3:9])([CH3:8])[CH3:6])=[CH:2][O:3][Si:7]([CH3:9])([CH3:8])[CH3:6]

Participants

4

Procedure

The preparation of the reagent 1,1,2-tris-trimethylsilyloxyethylene (80) is described hereinbelow in Flowsheet M. The reaction of glycolic acid with 1,1,1,3,3,3-hexamethyldisilazane and trimethylsilylchloride in pyridine gives bis-trimethylsilated glycolic acid (113). Addition of (113) to a tetrahydrofuran solution of one equivalent of lithium 1,1,1,3,3,3-hexamethyldisilazane amide at -78° C. generates a lithium enolate which is trapped with trimethylsilylchloride to produce the desired reagent (80). ##STR11##

Sources & evidence

ORD record
ord-70944fc12c8649f180fe3232505940cf
Source dataset
uspto-grants-1981_11
Patent number
US04299988

Reaction notes

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