Sulfuric Acid → HCID 178448155、化合物

HRID 1109687ノート

反応式

HRID 1109687 の反応式
[F:1][C:2]1[CH:3]=[C:4]([C@H:9]2[CH2:14][CH2:13][C@H:12]([CH:15]=[O:16])[CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[F:8].[CH:17](/[CH:20]([CH2:23]O)[CH2:21][OH:22])=[CH:18]\[CH3:19].S(=O)(=O)(O)O>C1(C)C=CC=CC=1>[CH:17](/[C@@H:20]1[CH2:21][O:22][C@@H:15]([C@H:12]2[CH2:11][CH2:10][C@H:9]([C:4]3[CH:5]=[CH:6][C:7]([F:8])=[C:2]([F:1])[CH:3]=3)[CH2:14][CH2:13]2)[O:16][CH2:23]1)=[CH:18]\[CH3:19]

参加物

5

反応物 3

HCID 1118Sulfuric AcidHCID 190192522-(1E-propenyl)-1,3-propanediolHCID 178520926HCID 178520926、化合物

生成物 1

HCID 178448155HCID 178448155、化合物収率 18.5%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

A solution of 3.0 g of trans-4-(3,4-difluorophenyl)cyclohexanecarboxaldehyde (prepared in accordance with Example 2) and 2.4 g of 2-(1E-propenyl)-1,3-propanediol in 75 ml of toluene was treated with 3 drops of 10 percent (v/v) sulphuric acid and the reaction mixture was heated to boiling for 1.25 hours, whereby moist toluene was distilled off and replaced by fresh toluene. Then, the reaction mixture was neutralized with triethylamine and, after cooling, washed three times with water, dried over sodium sulphate and concentrated. Chromatographic purification of the residue on 100 g of silica gel with hexane/ethyl acetate (vol. 49:1) and repeated recrystallization of the trans/cis mixture from hexane gave 0.8 g of pure trans-5-(1E-propenyl)-2-[trans-4-(3,4-difluoro-phenyl)cyclohexyl]-1,3-dioxane; m.p. (C-N) 96.0° C., cl.p. (N-I) 125.5° C., Δε (115° C.)=12.4.

後処理

  1. temperaturethe reaction mixture was heated
  2. distillationwhereby moist toluene was distilled off
  3. temperatureafter cooling
  4. washwashed three times with water
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated
  7. customChromatographic purification of the residue on 100 g of silica gel with hexane/ethyl acetate (vol. 49:1)
  8. customrecrystallization of the trans/cis mixture from hexane

出典と根拠

ORDレコード
ord-3616b99d5c19480eba18bf89782b76b5
出典データセット
uspto-grants-1994_06
特許番号
US05322638

反応ノート

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