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Dichloromethane → Ethyl 4-methyl-5-(2-oxaspiro[4.5]dec-7-en-8-yl)isoxazole-3-carboxylate

HRID 1478161
ノート
印刷プレビュー

反応式

HRID 1478161 の反応式
CC1(C)C(C)(C)OB([C:9]2[CH2:18][CH2:17][C:12]3([CH2:16][O:15][CH2:14][CH2:13]3)[CH2:11][CH:10]=2)O1.Br[C:21]1[O:25][N:24]=[C:23]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[C:22]=1[CH3:31].C([O-])([O-])=O.[Cs+].[Cs+].C(Cl)Cl>COCCOC.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:31][C:22]1[C:23]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[N:24][O:25][C:21]=1[C:9]1[CH2:18][CH2:17][C:12]2([CH2:16][O:15][CH2:14][CH2:13]2)[CH2:11][CH:10]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 6344DichloromethaneHCID 10796Cesium carbonateHCID 58828802Ethyl 5-bromo-4-methyl-1,2-oxazole-3-carboxylate2 回HCID 1312893314,4,5,5-Tetramethyl-2-(2-oxaspiro[4.5]dec-7-en-8-yl)-1,3,2-dioxaborolane

生成物 1

HCID 118511182Ethyl 4-methyl-5-(2-oxaspiro[4.5]dec-7-en-8-yl)isoxazole-3-carboxylate

試薬・触媒・溶媒 3

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
触媒
HCID 962Water溶媒
HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
90 °C

実験手順

[4,4,5,5-tetramethyl-2-(2-oxaspiro[4.5]dec-7-en-8-yl)-1,3,2-dioxaborolane] (0.172 g, 0.651 mmol), ethyl 5-bromo-4-methylisoxazole-3-carboxylate (Intermediate A) (0.183 g, 0.781 mmol) and Cs2CO3 (0.849 g, 2.60 mmol) were combined in DME (3 mL) and water (1.250 mL). PdCl2(dppf).CH2Cl2 adduct (0.016 g, 0.020 mmol) was added and the mixture was degassed thoroughly refilling with nitrogen. The mixture was stirred in the microwave at 90° C. for 1 hour. The biphasic reaction mixture was separated and the organic phase was adsorbed onto silica. Purification by chromatography eluting with a gradient of EtOAc in iso-hexane afforded the title compound;

後処理

  1. customthe mixture was degassed thoroughly
  2. customThe biphasic reaction mixture
  3. customwas separated
  4. customPurification by chromatography
  5. washeluting with a gradient of EtOAc in iso-hexane

出典と根拠

ORDレコード
ord-8ce6b326991b49dabf6ad5e0c9a70a2f
出典データセット
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09403810B2

反応ノート

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