Ammonium Chloride → Bis(4-methyl-5-thiazolyl)methanol

HRID 1377554노트

반응식

HRID 1377554 반응식
C([Li])CCC.[CH3:6][C:7]1[N:8]=[C:9]([Si](C)(C)C)[S:10][CH:11]=1.[CH3:16][C:17]1[N:18]=[CH:19][S:20][C:21]=1[CH:22]=[O:23].[Cl-].[NH4+]>O1CCCC1.C(OCC)C.CCCCC.O>[CH3:6][C:7]1[N:8]=[CH:9][S:10][C:11]=1[CH:22]([C:21]1[S:20][CH:19]=[N:18][C:17]=1[CH3:16])[OH:23]

참가 물질

7

반응물 4

HCID 25517Ammonium ChlorideHCID 5813394-Methylthiazole-5-carboxaldehydeHCID 116583544-Methyl-2-trimethylsilylthiazoleHCID 178418339Butyllithium

생성물 1

HCID 22106674Bis(4-methyl-5-thiazolyl)methanol

시약·촉매·용매 2

HCID 962Water용매HCID 86634712Tetrahydrofuran ether pentane용매

실험 절차

n-Butyllithium (2.5M solution in hexanes, 12.8 ml) was added dropwise to a stirred solution of 4-methyl-2-trimethylsilylthiazole (5 g) in anhydrous tetrahydrofuran/diethyl ether/pentane (4:4:1, 75 ml) at -100° C. under an atmosphere of dry nitrogen. After 90 minutes, 4-methyl-5-thiazolecarbaldehyde (J. Amer. Chem. Soc., 1982, 104, 4934-4943) (4 g) was added. After a further 3 hours at -100° C., water was added and the mixture was warmed to room temperature. Saturated aqueous ammonium chloride solution was added and the organic phase was separated, dried and evaporated. The residue was crystallised from ethyl acetate to give bis(4-methyl-5-thiazolyl)methanol. This material in dichloromethane was oxidised using manganese dioxide to give the title compound.

후처리

  1. waitAfter a further 3 hours at -100° C.
  2. customthe organic phase was separated
  3. customdried
  4. customevaporated
  5. customThe residue was crystallised from ethyl acetate

출처 및 근거

ORD 기록
ord-bf151e1ec0394f38bb4ec7d06729bbad
출처 데이터셋
uspto-grants-1997_09
특허 번호
US05665747

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