Water → Acetate

HRID 893559

반응식

HRID 893559 반응식
[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

참가 물질

6

반응물 3

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

생성물 2

HCID 175AcetateHCID 85570p-Toluenesulfonate

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

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 (Ac2O, Et3N, CH2Cl2) to provide the acetoxy-tosylate (the desired racemic acetate) in 93% yield. The diol route is illustrated as follows: ##STR3##

후처리

  1. customcould be prepared

출처 및 근거

ORD 기록
ord-43103bb205504cc5b58c81ebba3f1cb6
출처 데이터셋
uspto-grants-1992_06
특허 번호
US05126268

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