N,N,N',N'-Tetramethylethylenediamine → (3-Chloro-2-methoxymethoxyphenyl)(2-methoxyphenyl)methanol

HRID 1111278

反応式

HRID 1111278 の反応式
C([Li])CCC.CN(C)CCN(C)C.[Cl:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[O:21][CH2:22][O:23][CH3:24].[CH:25](=[O:34])[C:26]1[C:27]([O:32][CH3:33])=[CH:28][CH:29]=[CH:30][CH:31]=1.[Cl-].[NH4+]>O1CCCC1>[Cl:14][C:15]1[C:16]([O:21][CH2:22][O:23][CH3:24])=[C:17]([CH:25]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[O:32][CH3:33])[OH:34])[CH:18]=[CH:19][CH:20]=1

参加物

7

反応物 5

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 86582-MethoxybenzaldehydeHCID 25517Ammonium ChlorideHCID 5426241-Chloro-2-(methoxymethoxy)benzeneHCID 178418339Butyllithium

生成物 1

HCID 15679047(3-Chloro-2-methoxymethoxyphenyl)(2-methoxyphenyl)methanol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

A solution containing 69 ml of 1.6 N butyl lithium (0.11 mol) and 12.78 g (0.11 mol) of tetramethylethylenediamine was prepared under nitrogen and cooled to 0° C. To this was added, with stirring and cooling at 0° C., 16.83 g (0.098 mol) of 1-chloro-2-methoxymethoxybenzene. After 3 hours 13.34 g (0.098 mol) of o-anisaldehyde in 40 ml of anhydrous tetrahydrofuran was added slowly at 0°-5° C. and allowed to react. The product was then poured into a mixture of ice and saturated aqueous ammonium chloride and the resulting mixture was extracted with ether. The ether extract was dried over magnesium sulfate and then the volatiles were removed by evaporation under reduced pressure to obtain 29.3 g of crude title compound as a yellow solid. This was purified by preparative liquid chromatography eluting with a 10:90 mixture of acetone and hexane to obtain 21.1 g (70 percent of theory) of the title compound as a white solid melting at 89°-90° C. The proton nmr spectrum was consistent with the assigned structure.

後処理

  1. customwas prepared under nitrogen
  2. additionTo this was added
  3. temperaturecooling at 0° C.
  4. customto react
  5. extractionthe resulting mixture was extracted with ether
  6. extractionThe ether extract
  7. dry with materialwas dried over magnesium sulfate
  8. customthe volatiles were removed by evaporation under reduced pressure
  9. customto obtain 29.3 g of crude title compound as a yellow solid
  10. customThis was purified by preparative liquid chromatography
  11. washeluting with a 10:90 mixture of acetone and hexane

出典と根拠

ORDレコード
ord-ca88a6729c2b49019df8660a7ce15600
出典データセット
uspto-grants-1990_12
特許番号
US04979978

関連ノート

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