Sodium Carbonate → (2S,4aS,6aR,7R,9S,10aS,10bR)-9-(hydroxy)-2-(3-furanyl)dodecahydro-6a,10b-dimethyl-4,10-dioxo-2H-naphtho[2,1-c]pyran-7-carboxylic acid methyl ester

HRID 12313

반응식

HRID 12313 반응식
CC([O:4][C@@H:5]1[C:19](=[O:20])[C@H:18]2[C@@:8]([CH3:27])([CH2:9][CH2:10][C@@H:11]3[C@:17]2([CH3:21])[CH2:16][C@@H:15]([C:22]2[CH:23]=[CH:24][O:25][CH:26]=2)[O:14][C:12]3=[O:13])[C@H:7]([C:28]([O:30][CH3:31])=[O:29])[CH2:6]1)=O.C([O-])([O-])=O.[Na+].[Na+]>CO>[CH3:31][O:30][C:28]([C@@H:7]1[CH2:6][C@H:5]([OH:4])[C:19](=[O:20])[C@H:18]2[C@@:8]1([CH3:27])[CH2:9][CH2:10][C@H:11]1[C@:17]2([CH3:21])[CH2:16][C@@H:15]([C:22]2[CH:23]=[CH:24][O:25][CH:26]=2)[O:14][C:12]1=[O:13])=[O:29]

참가 물질

4

반응물 2

HCID 10340Sodium CarbonateHCID 128563Salvinorin A

생성물 1

HCID 11395172(2S,4aS,6aR,7R,9S,10aS,10bR)-9-(hydroxy)-2-(3-furanyl)dodecahydro-6a,10b-dimethyl-4,10-dioxo-2H-naphtho[2,1-c]pyran-7-carboxylic acid methyl ester수율 77%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A mixture of 1 (3.5 g, 8.0 mmol) and Na2CO3 (3.4 g, 32.2 mmol) in absolute MeOH (150 mL) was stirred at room temperature for 4 b. The solvent was removed under reduced pressure and CH2Cl2 (500 mL) was added to the crude residue. The organic extract was washed successively with 2N HCl (50 mL) and saturated NaCl (50 mL) and dried (Na2SO4). The solvent was removed under reduced pressure and MeOH (100 mL) was added to the residue. The resulting solid was collected by filtration and dried to afford 2.4 g (77%) of 8a as a white solid, mp 211-214° C. (Lit. 213-216° C.).

후처리

  1. customThe solvent was removed under reduced pressure and CH2Cl2 (500 mL)
  2. additionwas added to the crude residue
  3. extractionThe organic extract
  4. washwas washed successively with 2N HCl (50 mL) and saturated NaCl (50 mL)
  5. dry with materialdried (Na2SO4)
  6. customThe solvent was removed under reduced pressure and MeOH (100 mL)
  7. additionwas added to the residue
  8. filtrationThe resulting solid was collected by filtration
  9. customdried

출처 및 근거

ORD 기록
ord-520e1e20a5b74d83883664866993db0e
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07728001B2

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