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

HRID 1025733Notes

Reaction equation

HRID 1025733 reaction equation
[H-].[Na+].[CH2:3](Br)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[OH2:11].[CH3:12][CH2:13][O:14][C:15]([CH3:17])=[O:16]>CN(C=O)C>[CH2:3]([O:11][CH:4]1[CH2:5][CH2:6][C:15]2([O:16][CH2:12][CH2:13][O:14]2)[CH2:17][CH2:3]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 8857Ethyl AcetateHCID 24758Sodium hydride

Product 1

HCID 111394858-(Benzyloxy)-1,4-dioxaspiro[4.5]decane

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 1,4-dioxaspiro[4.5]decan-8-01 (1.18 g, 7.46 mmol) and NaH (0.358 g, 8.96 mmol) in DMF (5 mL) at 0° C. was added benzyl bromide (1.06 mL, 8.95 mmol). After being stirred overnight under N2, water and EtOAc were added. The aqueous layer was extracted with EtOAc (3×). The combined organic layers were dried (MgSO4), concentrated and flash chromatographed using 10% EtOAc/hexane to give 1.524 g of the title compound. MS (EI) calcd: (M+1)+=249.1; found: 249.2. 1H NMR (300 MHz, CDCl3) δ (ppm) 7.35 (5H, m), 4.52 (2H, s), 3.95 (4H, m), 3.5 (1H, m), 1.95-1.50 (8H, m).

Workup

  1. extractionThe aqueous layer was extracted with EtOAc (3×)
  2. dry with materialThe combined organic layers were dried (MgSO4)
  3. concentrationconcentrated
  4. customflash chromatographed

Sources & evidence

ORD record
ord-b11df79a9a4f4a7184a8c572a7d574b0
Source dataset
uspto-grants-2014_05
Patent number
US08729063B2

Reaction notes

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