Methanol → Methyl 4-tetrahydrofuran-3-ylsulfonylbenzoate

HRID 713064노트

반응식

HRID 713064 반응식
[O:1]1[CH2:5][CH2:4][CH:3]([S:6][C:7]2[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][CH:8]=2)[CH2:2]1.[OH2:17].OOS([O-])=O.[K+].C[OH:25]>>[O:1]1[CH2:5][CH2:4][CH:3]([S:6]([C:7]2[CH:8]=[CH:9][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:15][CH:16]=2)(=[O:25])=[O:17])[CH2:2]1

참가 물질

5

반응물 4

HCID 887MethanolHCID 962WaterHCID 23707502Potassium hydroxy sulfite2회HCID 68290908Methyl 4-tetrahydrofuran-3-ylsulfanylbenzoate

생성물 1

HCID 68291281Methyl 4-tetrahydrofuran-3-ylsulfonylbenzoate수율 93%

실험 절차

Methyl 4-tetrahydrofuran-3-ylsulfanylbenzoate (1.01 g, 4.24 mmol) was dissolved in methanol (25 mL), followed by the addition of water (2.5 mL), and Oxone (2.61 g, 4.24 mmol). The reaction mixture was stirred at room temperature for 24 hours. An additional 0.1 eq of Oxone (0.26 g) was added and the reaction mixture was stirred for 2 hours, then filtered and the solvent was concentrated in vacuo. The resulting residue was dissolved in dichloromethane (30 mL) and washed with water (2×25 mL). The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo to yield methyl 4-tetrahydrofuran-3-ylsulfonylbenzoate (1.07 g, 93%) as a yellow solid. ESI-MS m/z calc. 270.1. found 271.3 (M+1)+; Retention time: 1.02 minutes (3 min run).

후처리

  1. stirringthe reaction mixture was stirred for 2 hours
  2. filtrationfiltered
  3. concentrationthe solvent was concentrated in vacuo
  4. dissolutionThe resulting residue was dissolved in dichloromethane (30 mL)
  5. washwashed with water (2×25 mL)
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-df8f5ca20f5249fa8772575cf5abfa3e
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181273B2

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