Biisocrotyl → Tert-butyl 2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate

HRID 1182406

反応式

HRID 1182406 の反応式
[CH3:1][C:2](=[CH:4][CH:5]=[C:6]([CH3:8])[CH3:7])[CH3:3].[N+](=[CH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[N-]>>[CH3:7][C:6]1([CH3:8])[CH:5]([CH:4]=[C:2]([CH3:3])[CH3:1])[CH:11]1[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13]

参加物

3

反応物 2

HCID 12992BiisocrotylHCID 5097903Tert-butyl 2-diazoacetate

生成物 1

HCID 13379702Tert-butyl 2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate収率 89%

実験手順

In a 50 mL Schlenk tube purged with nitrogen, 22 mg of 2,2-bis[2-[(4S)-1-naphthyloxazoline]]propane was added to a white suspension containing 18 mg of cuprous trifluoromethanesulfonate and 5 mL of dichloroethane and stirred at a room temperature for 10 minutes to prepare a blue color homogeneous solution of an asymmetric copper complex. After that, 7.8 g of 2,5-dimethyl-2,4-hexadiene was added thereto and the inner temperature was adjusted to 40° C. and 1.4 g of tert-butyl diazoacetate was dropwise added for 2 hours and the resulting mixture was stirred at the same temperature further for 30 minutes to effect reaction and tert-butyl 2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate was obtained in a yield of 89% (based on tert-butyl diazoacetate). Trans-isomer/cis-isomer ratio=81/19. The optical purity of the trans-isomer was 86% e.e. and that of the cis-isomer was 60% e.e.

後処理

  1. customIn a 50 mL Schlenk tube purged with nitrogen, 22 mg of 2,2-bis[2-[(4S)-1-naphthyloxazoline]]propane
  2. additionwas added to a white suspension
  3. additioncontaining 18 mg of cuprous trifluoromethanesulfonate and 5 mL of dichloroethane
  4. customto prepare a blue color homogeneous solution of an asymmetric copper complex
  5. customwas adjusted to 40° C.
  6. stirringthe resulting mixture was stirred at the same temperature further for 30 minutes
  7. customreaction

出典と根拠

ORDレコード
ord-f7b399acfc5747909f203a849657e1ce
出典データセット
uspto-grants-2007_10
特許番号
US07288674B2

関連ノート

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