Sodium Bicarbonate → 1R-cis-Permethrinic acid

HRID 323923ノート

反応式

HRID 323923 の反応式
[CH3:1][C:2]1([CH3:13])[C@H:7]2[C@@H:3]1[C@H:4]([C:9](Cl)([Cl:11])[Cl:10])[O:5][C:6]2=[O:8].CC1(C)[C@H]2[C@@H]1[C@@H](C(Cl)(Cl)Cl)OC2=O.C(=O)([O-])O.[Na+].Cl.C(OC)(C)(C)C>CN(C=O)C>[Cl:10][C:9]([Cl:11])=[CH:4][C@H:3]1[C@@H:7]([C:6]([OH:8])=[O:5])[C:2]1([CH3:1])[CH3:13]

参加物

6

反応物 4

HCID 516892Sodium BicarbonateHCID 10538220(1R,4R,5S)-6,6-dimethyl-2-oxo-4-trichloromethyl-3-oxabicyclo[3.1.0]hexaneHCID 12525223(1R,4S,5S)-6,6-dimethyl-4-(trichloromethyl)-3-oxabicyclo[3.1.0]hexan-2-oneHCID 86756611tert-butylmethylether HCl

生成物 1

HCID 6736471R-cis-Permethrinic acid

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

A mixture of (1R,4R,5S)-6,6-dimethyl-4-(trichloromethyl)-3-oxabicyclo[3.1.0]hexan-2-one (I, R1=X1=X2=Cl) and (1R,4S,5S)-6,6-dimethyl-4-(trichloromethyl)-3-oxabicyclo[3.1.0]hexan-2-one (I, R1=X1=X2=Cl), 0.24 g (0.001 mol), is stirred with sodium hydrogen carbonate, 0.21 g (0.0025 mol), and Pd(C) 5%, 0.01 g, in about 4 ml of DMF at 50° C. under a hydrogen atmosphere of a slight overpressure. After stirring for ½ hour at 50° C. the mixture is stirred at room temperature. Samples taken out for GC analysis are treated with aqueous hydrochloric acid/methyl t-butyl ether and analysed on GC. After 16 hours GC analysis (area-%) shows a content of 39% of II and 32% of unreacted I. The retention time is identical to that of II prepared according to Ref.6, and MS (Mass (intensity in % of base peak): 208 (6) M+, 210 (4) (M+2)+, 175 (25), 173 (78), 165 (27), 163 (39), 111 (22), 109 (28), 91 (100), 77 (46), 39 (64)) is identical to MS of II prepared according to Ref.6.

後処理

  1. stirringis stirred at room temperature
  2. waitAfter 16 hours GC analysis (area-%) shows
  3. customprepared
  4. customprepared

出典と根拠

ORDレコード
ord-da76437e83b4464dac9176e69f47776c
出典データセット
uspto-grants-2001_04
特許番号
US06215023B1

反応ノート

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