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

HRID 346255

반응식

HRID 346255 반응식
[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]

참가 물질

5

반응물 3

HCID 6101p-Toluenesulfonic acidHCID 27716454-EthynylbenzaldehydeHCID 19990620HCID 19990620, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 241Benzene용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c9cf745b0adf40639ca7aee192e3a0dc
출처 데이터셋
uspto-grants-1991_10
특허 번호
US05061726

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