tert-Butyl bromoacetate → HCID 53800105, 화합물

HRID 383145노트

반응식

HRID 383145 반응식
[CH3:1][CH2:2][CH2:3][CH2:4][C:5]([O:7][CH3:8])=[S:6].C[Si]([N-][Si](C)(C)C)(C)C.[Na+].Br[CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22]>C1COCC1>[C:24]([O:23][C:21]([CH2:20][CH:4]([CH2:3][CH2:2][CH3:1])[C:5]([O:7][CH3:8])=[S:6])=[O:22])([CH3:27])([CH3:26])[CH3:25]

참가 물질

5

반응물 3

HCID 79177tert-Butyl bromoacetateHCID 560787o-Methyl pentanethioateHCID 2724254Sodium bis(trimethylsilyl)amide

생성물 1

HCID 53800105HCID 53800105, 화합물수율 49.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a −78° C. solution of methyl 4-methylthiobutyrate (1.48 g, 10.0 mmol) in THF (20 mL) was added sodium bis(trimethylsilyl)amide (1.0 M in THF, 11 mL). After 30 min, tert-butyl bromoacetate (2.34 g, 12.0 mmol) was added to the reaction, and the reaction mixture was gradually warmed to the room temperature over 6 hours. The reaction mixture was then partitioned between ethyl acetate (80 mL) and water (20 mL). The organic layer was washed with water (2×20 mL), brine (20 mL), dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by column chromatography with 5% ethyl acetate in hexane to give the title compound (1.21 g, 46%).

후처리

  1. customThe reaction mixture was then partitioned between ethyl acetate (80 mL) and water (20 mL)
  2. washThe organic layer was washed with water (2×20 mL), brine (20 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography with 5% ethyl acetate in hexane

출처 및 근거

ORD 기록
ord-eb4138a132ed4de1936a9b22ebe3d2d5
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06310095B1

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