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

HRID 905055

反応式

HRID 905055 の反応式
[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

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 8471Triethylamine触媒HCID 24813Phosphorus oxychloride触媒HCID 3283Diethyl Ether溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-963b87fab3af4ff0bf5eb899ec0cab23
出典データセット
uspto-grants-1983_12
特許番号
US04421758

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