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

HRID 1809893Notes

Reaction equation

HRID 1809893 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([OH:11])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[H-].[Na+].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O>CN(C=O)C.CCOC(C)=O>[CH2:14]([O:11][CH:8]1[CH2:9][CH2:10][C:5]2([O:4][CH2:3][CH2:2][O:1]2)[CH2:6][CH2:7]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 5673521,4-Dioxaspiro(4.5)decan-8-ol

Product 1

HCID 111394858-(Benzyloxy)-1,4-dioxaspiro[4.5]decaneYield 82.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 1,4-dioxaspiro[4.5]decan-8-ol (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-4032d61f6047429d9cab1d1157843d52
Source dataset
uspto-grants-2013_01
Patent number
US08362003B2

Reaction notes

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