Methyl chloroformate → 5-Methyl-4-triisopropylsilanyloxymethyl-furan-2-carboxylic acid methyl ester

HRID 490335노트

반응식

HRID 490335 반응식
[CH:1]([Si:4]([CH:16]([CH3:18])[CH3:17])([CH:13]([CH3:15])[CH3:14])[O:5][CH2:6][C:7]1[CH:11]=[CH:10][O:9][C:8]=1[CH3:12])([CH3:3])[CH3:2].C([Li])(CC)C.Cl[C:25]([O:27][CH3:28])=[O:26].[Cl-].[NH4+]>O1CCCC1>[CH3:28][O:27][C:25]([C:10]1[O:9][C:8]([CH3:12])=[C:7]([CH2:6][O:5][Si:4]([CH:1]([CH3:3])[CH3:2])([CH:13]([CH3:15])[CH3:14])[CH:16]([CH3:18])[CH3:17])[CH:11]=1)=[O:26]

참가 물질

6

반응물 4

HCID 6586Methyl chloroformateHCID 25517Ammonium ChlorideHCID 11043781Silane, tris(1-methylethyl)[(2-methyl-3-furanyl)methoxy]-HCID 178418400CID 53628100

생성물 1

HCID 588242025-Methyl-4-triisopropylsilanyloxymethyl-furan-2-carboxylic acid methyl ester

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of triisopropyl-(2-methyl-furan-3-ylmethoxy)-silane (14) (10.0 g) in tetrahydrofuran (300 mL) was cooled to −78° C. with stirring was treated drop-wise with sec-butyllithium (3.0 M in cyclohexane, 37 mL). After 1 hour the reaction mixture was treated drop-wise with a solution of methyl chloroformate (5.2 g) in tetrahydrofuran (30 mL) over 10 mins and stirring was continued at −78° C. for 1 hour. The reaction mixture was then treated with saturated ammonium chloride solution (300 mL) and allowed to warm to ambient temperature. The two layers were separated and the organic phase washed with brine (300 mL), dried and concentrated in vacuo. The residue was purified by flash chromatography eluting with ethyl acetate/pentane (1:9 by volume) to give compound 15 as a clear oil.

후처리

  1. stirringstirring
  2. customThe two layers were separated
  3. washthe organic phase washed with brine (300 mL)
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography
  7. washeluting with ethyl acetate/pentane (1:9 by volume)

출처 및 근거

ORD 기록
ord-277331fad4044dd2a6dd5ddd5c8d539e
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07528157B2

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