Dimethylformamide → HCID 10849075, compound

HRID 1742813Notes

Reaction equation

HRID 1742813 reaction equation
[H-].[Na+].CN(C=O)C.[CH3:8][C:9]1([CH3:19])[O:16][CH2:15][C@H:14]2[C@:12]([CH2:17][OH:18])([CH2:13]2)[CH2:11][O:10]1.[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[Cl-].[NH4+]>CCCCCC>[CH2:20]([O:18][CH2:17][C@:12]12[CH2:13][C@H:14]1[CH2:15][O:16][C:9]([CH3:19])([CH3:8])[O:10][CH2:11]2)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 10511391HCID 10511391, compound

Product 1

HCID 10849075HCID 10849075, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To a suspension of 1.2 g (30 mmol) of sodium hydride, previously washed with hexane, in 80 ml of DMF 4.07 g (23.6 mmol) of (1S,7R)-4,4-dimethyl-3,5-dioxabicyclo[5,1,0]oct-1-yl methanol was added and the mixture was stirred for 5 min. at room temperature. 3.97 ml (30 mmol) of benzyl bromide was added and the mixture was stirred for 14 hours at room temperature. Saturated aqueous solution of ammonium chloride was added and the mixture was extracted with hexane-ethyl acetate (1:1). The organic layer was washed with water and dried over anhydrous sodium sulfate, and evaporated in vacuo. The resultant residue was subjected to silica gel chromatography (hexane:ethyl acetate/5:1) to obtain 5.56 g (21.1 mmol, 90%) of (1S,7R)-1-benzyloxymethyl-4,4-dimethyl-3,5-dioxabicyclo[5,1,0]octane. Colorless oil; 1H-NMR(CDCl3) δ 0.67 (dd, J=4.2, 8.4 Hz, 1H), 0.92 (m, 1H), 1.00 (m, 1H), 1.28 (s,3H), 1.37 (s,3H), 3.13 (d, J=10.2 Hz, 1H), 3.50 (d, J=10.2 Hz, 1H), 3.70 (dd, J=3.9, 13.2 Hz, 1H), 3.78 (d, J=13.1 Hz, 1H), 4.12 (dd, J=5.1, 13.2 Hz, 1H), 4.15 (d, J=13.1 Hz, 1H), 4.50 (d, J =12.0 Hz, 1H), 4.55 (d, J=12.0 Hz, 1H), 7.32 (m, 5H); FD MASS, m/z 262 (M+).

Workup

  1. additionwas added
  2. stirringthe mixture was stirred for 14 hours at room temperature
  3. extractionthe mixture was extracted with hexane-ethyl acetate (1:1)
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-1c45e7981439456dbd02fef1694ef8a3
Source dataset
uspto-grants-1994_08
Patent number
US05342840

Reaction notes

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