Sodium Hydroxide → (4aR,7S,8aS)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-7-ol

HRID 1050248Notes

Reaction equation

HRID 1050248 reaction equation
C([O:9][C@@H:10]1[CH2:19][O:18][C@H:17]2[C@@H:12]([O:13][CH:14]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[O:15][CH2:16]2)[CH2:11]1)(=O)C1C=CC=CC=1.[OH-].[Na+].C(=O)(O)[O-].[Na+]>CO.C1COCC1>[C:20]1([CH:14]2[O:13][C@H:12]3[CH2:11][C@H:10]([OH:9])[CH2:19][O:18][C@@H:17]3[CH2:16][O:15]2)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 90044852(4aR,7S,8aS)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-7-yl benzoate

Product 1

HCID 58194975(4aR,7S,8aS)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-7-ol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of (4aR,7S,8aS)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-7-yl benzoate (650 mg, 1.910 mmol) in methanol (10 mL) and THF (5 mL) was added 5N aqueous NaOH (4.0 mL, 20.0 mmol). After 18 hours the mixture was poured into saturated aqueous sodium bicarbonate (100 mL) and extracted with EtOAc (2×120 mL). The combined organic layers were dried over sodium sulfate and concentrated under reduced pressure. The resultant white solid was chromatographed using a Biotage™ 25 g silica gel cartridge eluted with 0-100% EtOAc in 1:1 Hexane/DCM over 20 column volumes. The product fractions were combined and concentrated under reduced pressure to provide the title compound as a white solid. LC-MS: calculated for C13H16O4 236.10, observed m/e: 237.15 (M+H)+ (Rt 1.13/4 min).

Workup

  1. extractionextracted with EtOAc (2×120 mL)
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe resultant white solid was chromatographed
  5. washeluted with 0-100% EtOAc in 1:1 Hexane/DCM over 20 column volumes
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a385872de21d4092843cec12965dfdaf
Source dataset
uspto-grants-2016_07
Patent number
US09382243B2

Reaction notes

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