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

HRID 1377554ノート

反応式

HRID 1377554 の反応式
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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 86634712Tetrahydrofuran ether pentane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-bf151e1ec0394f38bb4ec7d06729bbad
出典データセット
uspto-grants-1997_09
特許番号
US05665747

反応ノート

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