Hydrochloric Acid → HCID 69098014, 화합물

HRID 1503078노트

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HRID 1503078 반응식
[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

참가 물질

9

반응물 4

HCID 313Hydrochloric AcidHCID 73012-MethyltetrahydrofuranHCID 54153109144728-22-3HCID 178418573HCID 178418573, 화합물

생성물 1

HCID 69098014HCID 69098014, 화합물

시약·촉매·용매 4

HCID 62652Cuprous chloride촉매HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 15413tert-Butyl methyl ether용매

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온도
-20 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-a0347d69968a45ba977e482e3d6ea224
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09212120B2

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