Benzoyl chloride → HCID 121396295, compound

HRID 60724Notes

Reaction equation

HRID 60724 reaction equation
[CH3:1][C:2]1([CH3:13])[O:6][C@@H:5]2[O:7][C@H:8]([CH:10]([OH:12])[CH3:11])[CH2:9][C@@H:4]2[O:3]1.[C:14](Cl)(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(Cl)Cl.CN(C1C=CN=CC=1)C.CCOC(C)=O>[C:14]([O:12][CH:10]([C@H:8]1[O:7][C@H:5]2[O:6][C:2]([CH3:1])([CH3:13])[O:3][C@H:4]2[CH2:9]1)[CH3:11])(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 2

HCID 7412Benzoyl chlorideHCID 1213963831-[(3aS,5S,6aS)-2,2-dimethyl-3a,5,6,6a-tetrahydro furo[2,3-d][1,3]dioxol-5-yl]ethanol2×

Product 1

HCID 121396295HCID 121396295, compoundYield 54.9%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a cooled solution of 1-[(3aS,5S,6aS)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]ethanol (compound 25g, 200 mg, 1.06 mmol) in DCM (8 mL) was added benzoyl chloride (178 mg, 1.28 mmol) and DMAP (259 mg, 2 mmol). After the addition, the mixture was warmed naturally to room temperature and stirred at room temperature overnight. The resulting mixture was diluted with EtOAc and washed with a saturated aqueous solution of NH4Cl. The organic layer was dried over Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography on silica gel (eluting with 1:3 EtOAc in petroleum ether) to afford 170 mg of 1-[(3aS,5S,6aS)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]ethyl benzoate (compound 25h).

Workup

  1. additionAfter the addition
  2. washwashed with a saturated aqueous solution of NH4Cl
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography on silica gel (eluting with 1:3 EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-47e223ba104c4b40ac8ca2f2cfdbdf11
Source dataset
uspto-grants-2016_09
Patent number
US09441008B2

Reaction notes

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