Sodium Hydroxide → (2E)-4-(tert-butoxy)-4-oxobut-2-enoic acid

HRID 1766135노트

반응식

HRID 1766135 반응식
[C:1]([O:5][C:6](=[O:14])/[CH:7]=[CH:8]/[C:9]([O:11]CC)=[O:10])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].[Li+].[Cl-].OS([O-])(=O)=O.[K+]>C1COCC1>[C:1]([O:5][C:6](=[O:14])/[CH:7]=[CH:8]/[C:9]([OH:11])=[O:10])([CH3:4])([CH3:2])[CH3:3]

참가 물질

6

반응물 4

HCID 14798Sodium HydroxideHCID 433294Lithium ChlorideHCID 516920Potassium bisulfateHCID 11469708HCID 11469708, 화합물

생성물 1

HCID 5797551(2E)-4-(tert-butoxy)-4-oxobut-2-enoic acid수율 82%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

4-1 (340 mg, 1.7 mmol) was stirred for 1 h at rt with a solution comprised of 4 mL THF, and 4 mL of a solution containing 1 M NaOH and 1 M LiCl. The resulting mixture was acidified to pH 3-4 with 1 M KHSO4 and extracted twice with 30 mL of EtOAc. The extract was washed with 30 mL of brine, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting material was subjected to silica gel flash chromatography using a gradient of 5–10% methanol in DCM to yield 240 mg (82% yield) of 4-2.

후처리

  1. extractionextracted twice with 30 mL of EtOAc
  2. washThe extract was washed with 30 mL of brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-85aa148c332a4591b2283321e9ae9c37
출처 데이터셋
uspto-grants-2007_06
특허 번호
US07230005B2

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