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Acetic Acid → 2-(Methoxymethyl)-4-thiazolecarboxaldehyde

HRID 1174128
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HRID 1174128 반응식
[CH3:1][O:2][CH2:3][C:4]1[S:5][CH:6]=[C:7]([C:9](OCC)=[O:10])[N:8]=1.CC(C[AlH]CC(C)C)C.C(O)(=O)C.C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+]>ClCCl>[CH3:1][O:2][CH2:3][C:4]1[S:5][CH:6]=[C:7]([CH:9]=[O:10])[N:8]=1
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참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 14487Diisobutylaluminum hydrideHCID 9855836Potassium sodium tartarateHCID 45117589Ethyl 2-(methoxymethyl)-1,3-thiazole-4-carboxylate

생성물 1

HCID 451217662-(Methoxymethyl)-4-thiazolecarboxaldehyde수율 99.9%

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매

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온도
-78 °C

실험 절차

A solution containing the product from Example 6C (7.4 g, 36.8 mmol) in dichloromethane (40 mL) was treated with DIBAL (73.6 mL, 1 M in dichloromethane) dropwise at −78° C. over 2 hours, stirred at −78° C. for 2 hours, treated with acetic acid (10 mL) at −78° C. and warmed to 25° C. A 10% solution of aqueous sodium potassium tartrate was added and the mixture was stirred vigorously for 1 hour. The reaction mixture was partitioned between chloroform and water. The organic phase was washed with brine, dried over MgSO4, filtered and concentrated. The residue was chromatographed on silica gel eluting with 0-100% ethyl acetate/dichloromethane to give the title compound (5.78 g, 71% yield).

후처리

  1. temperaturewarmed to 25° C
  2. stirringthe mixture was stirred vigorously for 1 hour
  3. customThe reaction mixture was partitioned between chloroform and water
  4. washThe organic phase was washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was chromatographed on silica gel eluting with 0-100% ethyl acetate/dichloromethane

출처 및 근거

ORD 기록
ord-c757adf5ec8845cbb1f882e44d411b16
출처 데이터셋
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07834043B2

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