2,4-Dichlorobenzyl alcohol → trans-6-(2,4-Dichlorobenzyloxy)-2-tosyloxymethyltetrahydropyran

HRID 905055

반응식

HRID 905055 반응식
[S:1]([O:11][CH2:12][CH:13]1[CH2:18][CH2:17][CH:16]=[CH:15][O:14]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[Cl:19][C:20]1[CH:27]=[C:26]([Cl:28])[CH:25]=[CH:24][C:21]=1[CH2:22][OH:23]>C(OCC)C.O=P(Cl)(Cl)Cl.C(N(CC)CC)C>[Cl:19][C:20]1[CH:27]=[C:26]([Cl:28])[CH:25]=[CH:24][C:21]=1[CH2:22][O:23][C@@H:15]1[O:14][C@@H:13]([CH2:12][O:11][S:1]([C:4]2[CH:5]=[CH:6][C:7]([CH3:8])=[CH:9][CH:10]=2)(=[O:3])=[O:2])[CH2:18][CH2:17][CH2:16]1

참가 물질

6

반응물 2

HCID 156842,4-Dichlorobenzyl alcoholHCID 13071283(3,4-dihydro-2H-pyran-2-yl)methyl 4-methylbenzene-1-sulfonate

생성물 1

HCID 13073916trans-6-(2,4-Dichlorobenzyloxy)-2-tosyloxymethyltetrahydropyran수율 81.8%

시약·촉매·용매 3

HCID 8471Triethylamine촉매HCID 24813Phosphorus oxychloride촉매HCID 3283Diethyl Ether용매

실험 절차

To a solution of 1.34 g of 2-tosyloxymethyl-3,4-dihydro-2H-pyran in 25 ml of diethyl ether were added 1.06 g of 2,4-dichlorobenzyl alcohol, followed by a catalytic amount (2-3 drops) of phosphorus oxytrichloride. The mixture was then stirred at room temperature for 4 days, after which 3 drops of triethylamine were added to the mixture, which was then concentrated by evaporation under reduced pressure. The residue was purified by column chromatography through silica gel as in Example 1(a), to give 1.82 g of trans-6-(2,4-dichlorobenzyloxy)-2-tosyloxymethyltetrahydropyran (having the lesser polarity), 144 mg of cis-6-(2,4-dichlorobenzyloxy)-2-tosyloxymethyltetrahydropyran (having the greater polarity) and 200 mg of a cis/trans mixture.

후처리

  1. concentrationwas then concentrated by evaporation under reduced pressure
  2. customThe residue was purified by column chromatography through silica gel as in Example 1(a)

출처 및 근거

ORD 기록
ord-963b87fab3af4ff0bf5eb899ec0cab23
출처 데이터셋
uspto-grants-1983_12
특허 번호
US04421758

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