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

HRID 2286353Notes

Reaction equation

HRID 2286353 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

Reactant 2

HCID 757Glycolic AcidHCID 6397Chlorotrimethylsilane

Product 1

HCID 553067(Vinyl-2-ylidenetris(oxy))tris(trimethylsilane)

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The preparation of the reagent 1,1,2-tris-tri-C1 to C4 alkylsilyloxyethylene is described below using, as the illustrative compound 1,1,2-tris-trimethylsilyloxyethylene (80). The reaction of glycolic acid with 1,1,1,3,3,3-hexamethyldisilazane and trimethylsilylchloride in pyridine gives bis-trimethylsilated glycolic acid (113), see Flowsheet M. 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). ##STR57##

Sources & evidence

ORD record
ord-40657d9196fe43f38c901ba1e845a4ac
Source dataset
uspto-grants-1981_05
Patent number
US04265904

Reaction notes

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