Hydrochloric Acid → HCID 69098014、化合物

HRID 1503078ノート

反応式

HRID 1503078 の反応式
[CH2:1]1[C:3]2([CH2:8][C:7](=[O:9])[O:6][C:5](=[O:10])[CH2:4]2)[CH2:2]1.[CH3:11][Mg]Br.CC1CCCO1.Cl>O1CCCC1.[Cu]Cl.C(OC)(C)(C)C.O>[O:9]=[C:7]([CH3:11])[CH2:8][C:3]1([CH2:4][C:5]([OH:6])=[O:10])[CH2:2][CH2:1]1

参加物

9

反応物 4

HCID 313Hydrochloric AcidHCID 73012-MethyltetrahydrofuranHCID 54153109144728-22-3HCID 178418573HCID 178418573、化合物

生成物 1

HCID 69098014HCID 69098014、化合物

試薬・触媒・溶媒 4

HCID 62652Cuprous chloride触媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒HCID 15413tert-Butyl methyl ether溶媒

反応条件

温度
-20 °C

実験手順

To a solution of 4.4 g 6-oxa-spiro[2.5]octane-5,7-dione (31 mmole) in 66 ml tetrahydrofuran are added 600 mg copper(I)chloride (6 mmole, 0.2 eq). The mixture is cooled to −20° C. and 9.8 ml of methylmagnesium bromide in 2-methyl tetrahydrofuran (3.2 M solution in 2-methyl tetrahydrofuran, 31 mmole, 1.0 eq) are added dropwise over 0.5 hours. The mixture is warmed to room temperature and stirred for 2 hours. 66 ml of water are added and the mixture is acidified to pH 3.0 by addition of 20.4 g of 2 M hydrochloric acid. 50 ml of methyl tert-butyl ether are added and the phases are separated. The aqueous phase is extracted again with 50 ml of methyl tert-butyl ether and the combined organic phases are washed with 20 ml of brine and concentrated to dryness. The resulting crude product is directly used in the next step (esterification to [1-(2-oxo-propyl)-cyclopropyl]-acetic acid methyl ester).

後処理

  1. temperatureThe mixture is warmed to room temperature
  2. customthe phases are separated
  3. extractionThe aqueous phase is extracted again with 50 ml of methyl tert-butyl ether
  4. washthe combined organic phases are washed with 20 ml of brine
  5. concentrationconcentrated to dryness

出典と根拠

ORDレコード
ord-a0347d69968a45ba977e482e3d6ea224
出典データセット
uspto-grants-2015_12
特許番号
US09212120B2

反応ノート

読み込み中…