Hydrochloric Acid → Diethyl 2-(4-(4-chlorophenyl)-tetrahydro-2H-pyran-4-carbonyl)malonate

HRID 2078032

반응식

HRID 2078032 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:14]([OH:16])=O)[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.[C:23]([O:31][CH2:32][CH3:33])(=[O:30])[CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26].[Mg+2].[Cl-].[Cl-].C([O-])(=O)CC([O-])=O.Cl>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([C:14]([CH:24]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:23]([O:31][CH2:32][CH3:33])=[O:30])=[O:16])[CH2:9][CH2:10][O:11][CH2:12][CH2:13]2)=[CH:6][CH:7]=1

참가 물질

8

반응물 6

HCID 313Hydrochloric AcidHCID 7761Diethyl MalonateHCID 9084Malonate IonHCID 65578Oxalyl chlorideHCID 5360315Magnesium ChlorideHCID 167665834-(4-Chlorophenyl)oxane-4-carboxylic acid

생성물 1

HCID 67100011Diethyl 2-(4-(4-chlorophenyl)-tetrahydro-2H-pyran-4-carbonyl)malonate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 4-(4-chlorophenyl)tetrahydro-2H-pyran-4-carboxylic acid (0.500 g, 2.08 mmol) in IPAc (2.5 mL) was added DMF (0.050 mL). Oxalyl chloride (0.277 g, 0.19 mL, 2.18 mmol) was then added at ambient temperature over a period of 20 minutes. The resulting solution was stirred at room temperature for a period of 2 hours. In a separate flask, a solution of diethyl malonate (0.420 g, 0.40 mL, 2.60 mmol) in IPAc (3.5 mL) was treated with MgCl2 (0.247 g, 2.60 mmol). The resulting slurry was aged at room temperature for 30 minutes and subsequently treated with TEA (0.704 g, 0.97 mL, 2.60 mmol). After a further 2 hours at ambient temperature, the malonate slurry was cooled to 5° C. and treated with the acyl chloride solution. The resulting mixture was aged at room temperature for 2 hours then treated with a 5N HCl solution (2.5 mL). The organic layer was separated, and the aqueous layer was extracted 3 times with IPAc (2.5 mL). The organic phases were combined, dried (MgSO4), and concentrated under reduced pressure to afford the title compound as an orange oil. MS m/e=383.2 (M+H)+.

후처리

  1. waitThe resulting slurry was aged at room temperature for 30 minutes
  2. waitAfter a further 2 hours at ambient temperature
  3. waitThe resulting mixture was aged at room temperature for 2 hours
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted 3 times with IPAc (2.5 mL)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-c3d52b62815943fbb17920ad60224b3e
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07928139B2

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