p-Toluenesulfonic acid → 5-t-Butyl-2-(4-ethynylphenyl)-1,3-oxathiane

HRID 346255

反応式

HRID 346255 の反応式
[CH3:1][C:2]([CH3:9])([CH3:8])[CH:3]([CH2:6][SH:7])[CH2:4][OH:5].[C:10]([C:12]1[CH:19]=[CH:18][C:15]([CH:16]=O)=[CH:14][CH:13]=1)#[CH:11].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[C:2]([CH:3]1[CH2:4][O:5][CH:16]([C:15]2[CH:18]=[CH:19][C:12]([C:10]#[CH:11])=[CH:13][CH:14]=2)[S:7][CH2:6]1)([CH3:9])([CH3:8])[CH3:1]

参加物

5

反応物 3

HCID 6101p-Toluenesulfonic acidHCID 27716454-EthynylbenzaldehydeHCID 19990620HCID 19990620、化合物

生成物 1

HCID 199906265-t-Butyl-2-(4-ethynylphenyl)-1,3-oxathiane

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

実験手順

A solution of 3,3-dimethyl-2-mercaptomethylbutan-1-ol (1.46 g), 4-ethynylbenzaldehyde (1.30 g) (W.B. Austin et al. J. Org. Chem., 1981, 46. 2280) and para-toluenesulphonic acid (10 mg) in benzene (50 ml) was heated to reflux overnight under Dean and Stark conditions. The resulting solution was evaporated under reduced pressure and the residue was purified on silica. Elution with 4:1 hexane: dichloromethane gave 5-t-butyl-2-(4-ethynylphenyl)-1,3-oxathiane as a mixture of isomers.

後処理

  1. temperatureto reflux overnight under Dean and Stark conditions
  2. customThe resulting solution was evaporated under reduced pressure
  3. customthe residue was purified on silica
  4. washElution with 4:1 hexane

出典と根拠

ORDレコード
ord-c9cf745b0adf40639ca7aee192e3a0dc
出典データセット
uspto-grants-1991_10
特許番号
US05061726

関連ノート

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