Water → 8-(Benzyloxymethyl)-1,4-dioxaspiro[4.5]decane

HRID 1960026Notes

Reaction equation

HRID 1960026 reaction equation
[H-].[Na+].[O:3]1[C:7]2([CH2:12][CH2:11][CH:10]([CH2:13][OH:14])[CH2:9][CH2:8]2)[O:6][CH2:5][CH2:4]1.[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.O>CN(C=O)C.CCOC(C)=O>[CH2:15]([O:14][CH2:13][CH:10]1[CH2:11][CH2:12][C:7]2([O:6][CH2:5][CH2:4][O:3]2)[CH2:8][CH2:9]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 962Water2×HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 100808381,4-Dioxaspiro[4.5]decan-8-ylmethanol

Product 1

HCID 103780318-(Benzyloxymethyl)-1,4-dioxaspiro[4.5]decane

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of NaH (60% in oil, 60.9 g, 1.52 mol) in DMF (1500 mL) is carefully added crude (1,4-dioxa-spiro[4.5]dec-8-yl)methanol (15 g) in DMF (50 mL) at 10° C. under argon atmosphere and the mixture is stirred for 1 hour at the same temperature. To the mixture is added benzyl bromide (181 mL) 10° C., and stirring is continued for 3 hours at room temperature. After addition of H2O (70 mL) over 10 min, the mixture is poured into the mixture of H2O (4500 mL) and EtOAc (2000 mL). The water layer is extracted with EtOAc and the combined organic layer is washed with brine, dried over magnesium sulfate, and concentrated under reduced pressure to afford crude 8-benzyloxymethyl-1,4-dioxa-spiro[4.5]decane as a yellow oil. The crude product is used without further purification.

Workup

  1. stirringstirring
  2. waitis continued for 3 hours at room temperature
  3. extractionThe water layer is extracted with EtOAc
  4. washthe combined organic layer is washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a88a1e659c47450292fbd852c7553596
Source dataset
uspto-grants-2013_04
Patent number
US08410275B2

Reaction notes

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