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

HRID 399107Notes

Reaction equation

HRID 399107 reaction equation
[H-].[Na+].[CH2:3]1[O:13][C:6]2([CH:11](O)[CH2:10][CH2:9][CH2:8][CH2:7]2)[O:5][CH2:4]1.[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.CN(C=[O:26])C>[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:3]1[O:13][C:6]2([CH2:11][CH2:10][CH:9]([O:26][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:8][CH2:7]2)[O:5][CH2:4]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 5673631,4-Dioxaspiro[4.5]decan-6-ol

Product 1

HCID 111394858-(Benzyloxy)-1,4-dioxaspiro[4.5]decaneYield 70%

Reagents, catalysts & solvents 1

HCID 67553Tetrabutylammonium IodideCatalyst

Conditions

Temperature
65 °C

Procedure

Sodium hydride (60% oil dispersion, 2.2 g, 56 mmol) was added in portions to a solution of 6-hydroxycyclohexanone ethylene ketal (39) (8.8 g, 51 mmol), benzyl bromide (9.6 g, 5.6 mmol), and tetra-n-butylammonium iodide (50 mg) in dry DMF (50 mL) at 25° C. (Step 36). The mixture was stirred for 1 hr at 65° C., poured over ice and then extracted with ether (2×50 mL). The combined ether extract was washed with water (3×50 mL), dried (MgSO4) and solvent was removed. Chromatography on silica gel using 10:90 ethyl acetate/hexane (Rf=0.39) afforded 8.9 g (70%) of the benzyl ether 40. 1H NMR (CDCl3) δ1.6-1.9 (m, 8H, ring-CH2), 3.6 (m, 1H, CH--O), 4.0 (2, 4H, ketal-CH2), 4.6 (s, 2H, CH2 --O).

Workup

  1. additionpoured over ice
  2. extractionextracted with ether (2×50 mL)
  3. extractionThe combined ether extract
  4. washwas washed with water (3×50 mL)
  5. dry with materialdried (MgSO4) and solvent
  6. customwas removed

Sources & evidence

ORD record
ord-5566061ef10845e69dc09314949e4440
Source dataset
uspto-grants-1998_10
Patent number
US05817776

Reaction notes

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