Water → HCID 86650297, 화합물

HRID 1628130노트

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HRID 1628130 반응식
[CH3:1][S:2]([O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][S:14]C(=O)C)=[CH:8][CH:7]=1)(=[O:4])=[O:3].[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[SH:14][CH2:13][CH2:12][C:9]1[CH:8]=[CH:7][C:6]([O:5][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:11][CH:10]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydride2회HCID 86650296S-[2-[4-[(Methylsulfonyl)oxy]phenyl]ethyl] ethanethioate

생성물 1

HCID 86650297HCID 86650297, 화합물수율 109.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
50 °C

실험 절차

Thioacetic acid S-[2-(4-methanesulfonyloxy-phenyl)-ethyl]ester (250 mg, 0.91 mmol) was dissolved in anhydrous THF (2.5 mL) and LiAlH4 (38 mg, 1.0 mmol) was added in portions. After completed addition the mixture was warmed up to 50° C. and stirred for 1.5 h. The mixture was cooled down to 0° C. and excess LiAlH4 was hydrolyzed by the addition of H2O (0.8 mL), 2N aq. NaOH (1.0 mL) and THF (10 mL). Afterwards the reaction mixture was refluxed for 30 min then the precipitated salts were filtered off and the remaining filtrated was diluted with EtOAc. After extraction with brine and drying over Na2SO4, the solvent was evaporated under reduced pressure to afford the crude product as an oil (232 mg, 94.9%). 1H NMR (400 MHz, CDCl3): δ 7.29-7.31 (d, 2H), 7.21-7.23 (d, 2H), 3.31 (s, 3H), 2.81-2.85 (m, 2H), 2.68-2.73 (m, 2H).

후처리

  1. additionaddition the mixture
  2. temperatureThe mixture was cooled down to 0° C.
  3. temperatureAfterwards the reaction mixture was refluxed for 30 min
  4. filtrationthe precipitated salts were filtered off
  5. filtrationthe remaining filtrated
  6. additionwas diluted with EtOAc
  7. extractionAfter extraction with brine
  8. dry with materialdrying over Na2SO4
  9. customthe solvent was evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-2302b6a7c0404c47835b5dded7842c7d
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08785681B2

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