Sodium Bicarbonate → 1R-cis-Permethrinic acid

HRID 323923노트

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HRID 323923 반응식
[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]

참가 물질

6

반응물 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

생성물 1

HCID 6736471R-cis-Permethrinic acid

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
50 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-da76437e83b4464dac9176e69f47776c
출처 데이터셋
uspto-grants-2001_04
특허 번호
US06215023B1

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