Water → HCID 58550271, compound

HRID 2068873Notes

Reaction equation

HRID 2068873 reaction equation
[H-].[Na+].[CH2:3](Br)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH2:11]([O:13][CH2:14][CH3:15])[CH3:12].[OH2:16].CN(C)[CH:19]=[O:20]>>[CH2:3]([O:20][CH2:19][C:5]1([CH3:6])[CH2:4][CH2:9][CH2:8][C:11]2([O:16][CH2:15][CH2:14][O:13]2)[CH2:12]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 5

HCID 962WaterHCID 3283Diethyl EtherHCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 24758Sodium hydride

Product 1

HCID 58550271HCID 58550271, compoundYield 93%

Procedure

Under a nitrogen atmosphere, to a solution of (7-methyl-1,4-dioxaspiro[4.5]deca-7-yl)methanol (4.0 g, 21 mmol) in N,N-dimethylformamide (40 ml) was added sodium hydride (1.1 g, 27 mmol) under ice-cooling, and the mixture was stirred for 30 min. Then, to the reaction mixture was added benzyl bromide (3.1 ml, 25 mmol) at room temperature, and the mixture was further stirred for 1 hr. To the reaction mixture were added diethyl ether and water, and the organic layer was separated. Then, the organic layer was washed successively with water and saturated brine, and dried over sodium sulfate. Sodium sulfate was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography to give the title compound (5.7 g, yield 93%).

Workup

  1. temperaturecooling
  2. stirringthe mixture was further stirred for 1 hr
  3. customthe organic layer was separated
  4. washThen, the organic layer was washed successively with water and saturated brine
  5. dry with materialdried over sodium sulfate
  6. customSodium sulfate was removed by filtration
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-6e37aaa18984416785cb6544a7c92238
Source dataset
uspto-grants-2012_10
Patent number
US08299070B2

Reaction notes

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