Benzenemethanol, 2,6-dichloro- → trans-6-(2,6-Dichlorobenzyloxy)-2-tosyloxymethyltetrahydropyran

HRID 905058

反応式

HRID 905058 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]=[CH:26][CH:25]=[C:24]([Cl:28])[C:21]=1[CH2:22][OH:23]>C(OCC)C.O=P(Cl)(Cl)Cl>[Cl:19][C:20]1[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[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

5

反応物 2

HCID 27156Benzenemethanol, 2,6-dichloro-HCID 13071283(3,4-dihydro-2H-pyran-2-yl)methyl 4-methylbenzene-1-sulfonate

生成物 1

HCID 54030357trans-6-(2,6-Dichlorobenzyloxy)-2-tosyloxymethyltetrahydropyran収率 71.1%

試薬・触媒・溶媒 2

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 and 1.06 g of 2,6-dichlorobenzyl alcohol in 25 ml of diethyl ether was added a catalytic amount (2 drops) of phosphorus oxytrichloride, and then the mixture was stirred at room temperature for 4 days. The colourless crystals which had precipitated were filtered off, giving 1.582 g of trans-6-(2,6-dichlorobenzyloxy)-2-tosyloxymethyltetrahydropyran, melting at 123°-124° C. Triethylamine was then added to the mother liquor and the resulting mixture was evaporated under reduced pressure and the residue purified by column chromatography through silica gel, in essentially the same manner as described in Example 1(a), to give 338 mg of trans-6-(2,6-dichlorobenzyloxy)-2-tosyloxymethyltetrahydropyran and 306 mg of cis-6-(2,6-dichlorobenzyloxy)-2-tosyloxymethyltetrahydropyran.

後処理

  1. customThe colourless crystals which had precipitated
  2. filtrationwere filtered off

出典と根拠

ORDレコード
ord-89332c3cc6314095a42f066bc7580a28
出典データセット
uspto-grants-1983_12
特許番号
US04421758

関連ノート

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