Water → HCID 131735802, compound

HRID 2205175Notes

Reaction equation

HRID 2205175 reaction equation
[CH2:1]([O:8][C@H:9]1[C@@H:16]2[C@@H:12]([O:13][C:14](C)([CH3:17])[O:15]2)[O:11][C@@:10]1([CH2:22][O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH:19]([F:21])[F:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[CH3:32][C:33]([O:35]C(C)=O)=[O:34]>CC(O)=O.OS(O)(=O)=O>[C:14]([O:13][CH:12]1[C@H:16]([O:35][C:33](=[O:34])[CH3:32])[C@H:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C@:10]([CH2:22][O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)([CH:19]([F:20])[F:21])[O:11]1)(=[O:15])[CH3:17]

Participants

6

Reactant 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 118294322HCID 118294322, compound

Product 1

HCID 131735802HCID 131735802, compound

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of compound (3aR,5R,6S,6aR)-6-(benzyloxy)-5-(benzyloxymethyl)-5-(difluoromethyl)-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxole (1.0 g, 6.3 mmol) in Ac2O (2.5 mL) and AcOH (10 mL) was added H2SO4 (3 drops). The mixture was stirred at room temperature for 3 hrs. TLC showed the reaction was complete. The mixture was poured to water, extracted with EtOAc, dried (Na2SO4) and purified by silica gel chromatography [ethyl acetate:petroleum ether (1:3)] to afford compound 5 (1.0 g, crude) as a light-color oil. LC-MS (M+H)+=465.1

Workup

  1. extractionextracted with EtOAc
  2. dry with materialdried (Na2SO4)
  3. custompurified by silica gel chromatography [ethyl acetate:petroleum ether (1:3)]

Sources & evidence

ORD record
ord-06a8db548cc14ac0b096e5565cee5367
Source dataset
uspto-grants-2016_06
Patent number
US09370569B2

Reaction notes

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