Benzoyl chloride → ((5S,6aR)-2,2,6a-trimethyl-dihydro-5H-furo[3,2-d][1,3]dioxol-5-yl)methyl benzoate

HRID 409010Notes

Reaction equation

HRID 409010 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:10][C:11]1([CH3:22])[O:15][C@:14]2([CH3:21])[CH2:16][C@@H:17]([CH2:19][OH:20])[O:18][CH:13]2[O:12]1>N1C=CC=CC=1.CN(C1C=CN=CC=1)C>[C:1]([O:20][CH2:19][C@H:17]1[O:18][CH:13]2[C@:14]([CH3:21])([O:15][C:11]([CH3:22])([CH3:10])[O:12]2)[CH2:16]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 7412Benzoyl chlorideHCID 66780018((5S,6aR)-2,2,6a-trimethyl-dihydro-5H-furo[3,2-d][1,3]dioxol-5-yl)methanol

Product 1

HCID 66778757((5S,6aR)-2,2,6a-trimethyl-dihydro-5H-furo[3,2-d][1,3]dioxol-5-yl)methyl benzoateYield 101.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

Benzoyl chloride (1.92 mL, 0.0166 mol) was added to a solution of ((5S,6aR)-2,2,6a-trimethyl-dihydro-5H-furo[3,2-d][1,3]dioxol-5-yl)methanol (from step 8) (2.72 g, 0.0138 mol) in 20 mL of anhydrous pyridine at 0° C. To this mixture 5 mol % of DMAP was added and stirred at room temperature for 3 h. Pyridine was removed under vacuum; the residue was diluted with ethyl acetate and washed with 1N HCl, saturated NaHCO3 and brine. The organic layers were dried over anhydrous Na2SO4, filtered and concentrated. The compound was purified via column chromatography using hexane and ethyl acetate as a gradient mixture to give 4.1 g of the title compound (97% yield).

Workup

  1. customPyridine was removed under vacuum
  2. additionthe residue was diluted with ethyl acetate
  3. washwashed with 1N HCl, saturated NaHCO3 and brine
  4. dry with materialThe organic layers were dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe compound was purified via column chromatography

Sources & evidence

ORD record
ord-bb4ab9e4b4c24512bb21334f1e6e3a19
Source dataset
uspto-grants-2014_06
Patent number
US08759318B2

Reaction notes

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