Water → Acetate

HRID 893557

Reaction equation

HRID 893557 reaction equation
[OH:1]C[CH:3]([OH:6])[CH:4]=C.O.[C:8]1([CH3:18])[CH:13]=[CH:12][C:11]([S:14](Cl)(=[O:16])=[O:15])=[CH:10][CH:9]=1>N1C=CC=CC=1>[C:3]([O-:6])(=[O:15])[CH3:4].[CH3:18][C:8]1[CH:13]=[CH:12][C:11]([S:14]([O-:1])(=[O:16])=[O:15])=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 103383-Butene-1,2-diol

Product 2

HCID 175AcetateHCID 85570p-Toluenesulfonate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The racemic acetate substrate was prepared by one of two methods. The diol route began with racemic 1,2-dihydroxy-3-butene which could be prepared by reacting EpB with water under neutral conditions or with acid catalysis. The diol was treated with p-toluenesulfonyl chloride (p-TsCl) in pyridine at 4° C. to afford the desired monotosylate contaminated with about 10% of the corresponding ditosylate. The monotosylate could be selectively crystallized to afford pure monotosylate in 61% yield. Hydroxytosylate was acetylated under normal conditions (Ac20, Et3N, CH2C12) to provide the acetoxy-tosylate (the desired racemic acetate) in 93% yield. The diol route is illustrated as follows: ##STR3##

Workup

  1. customcould be prepared

Sources & evidence

ORD record
ord-3662bb7299724c8fb768ba863230b39b
Source dataset
uspto-grants-1992_06
Patent number
US05126267

Linked notes

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