Acetyl chloride → (RS)alpha-cyano-3-phenoxy-benzyl(1R,cis)2,2-dimethyl-3-(3-oxo-3-methoxymethoxy-1propynyl)-cyclopropane-carboxylate

HRID 569519

反応式

HRID 569519 の反応式
[CH3:1][C:2]1([CH3:29])[C@@H:4]([C:5]#[C:6][C:7]([OH:9])=[O:8])[C@H:3]1[C:10]([O:12][CH:13]([C:27]#[N:28])[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:15]=1)=[O:11].[H-].[Na+].Cl[CH2:33][O:34][CH2:35]Cl.COCOC.C(Cl)(=O)C.P(O)(O)([O-])=O.[Na+]>CN(C)C=O.CO>[CH3:1][C:2]1([CH3:29])[C@@H:4]([C:5]#[C:6][C:7](=[O:9])[O:8][CH2:33][O:34][CH3:35])[C@H:3]1[C:10]([O:12][CH:13]([C:27]#[N:28])[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:15]=1)=[O:11]

参加物

9

反応物 6

HCID 6367Acetyl chlorideHCID 8020DimethoxymethaneHCID 10967Bis(Chloromethyl) EtherHCID 24758Sodium hydrideHCID 23672064Monosodium phosphateHCID 53972231(RS)alpha-cyano-3-phenoxy-benzyl(1R,cis)2,2-dimethyl-3-(3-hydroxy-3-oxo-1-propynyl)-cyclopropane-carboxylate

生成物 1

HCID 54503448(RS)alpha-cyano-3-phenoxy-benzyl(1R,cis)2,2-dimethyl-3-(3-oxo-3-methoxymethoxy-1propynyl)-cyclopropane-carboxylate

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6228Dimethylformamide溶媒

実験手順

A solution of 3 g of (RS)α-cyano-3-phenoxy-benzyl(1R,cis)2,2-dimethyl-3-(3-hydroxy-3-oxo-1-propynyl)-cyclopropane-carboxylate in 30 ml of anhydrous dimethylformamide was cooled to +10° C. and 300 mg of 61% sodium hydride in oil were added in portions thereto. Then, over 15 minutes, 2.5 ml of chloromethyl ether solution prepared by mixing 4.5 ml of methylal and 0.52 ml of methanol and slowly adding 3.53 ml of acetyl chloride after which the mixture was stirred for 36 hours at room temperature. The mixture was stirred for 2 hours and was then poured into an aqueous solution of monosodium phosphate. The mixture was extracted with ethyl acetate and the organic phase was washed with water, dried and evaporated to dryness. The residue was chromatographed over silica gel and eluted with a 75-25 mixture of cyclohexane-ethyl acetate to obtain 2 g of (RS)α-cyano-3-phenoxy-benzyl(1R,cis)2,2-dimethyl-3-(3-oxo-3-methoxymethoxy-1propynyl)-cyclopropane-carboxylate.

後処理

  1. stirringThe mixture was stirred for 2 hours
  2. extractionThe mixture was extracted with ethyl acetate
  3. washthe organic phase was washed with water
  4. customdried
  5. customevaporated to dryness
  6. customThe residue was chromatographed over silica gel
  7. washeluted with a 75-25 mixture of cyclohexane-ethyl acetate

出典と根拠

ORDレコード
ord-6993c52a9709414f9a845b75bea54f55
出典データセット
uspto-grants-1988_03
特許番号
US04732903

関連ノート

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