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

HRID 1520708Notes

Reaction equation

HRID 1520708 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>O1CCCC1>[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

5

Reactant 3

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 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of sodium hydride (60% oil dispersion) (8.86 g) in tetrahydrofuran (170 mL) was added a solution of EXAMPLE 531B (30.52 g) in tetrahydrofuran (100 mL). This mixture was stirred for 30 minutes and benzyl bromide (24 mL) was added. After stirring for 72 hours, the reaction was quenched with saturated aqueous ammonium chloride solution (400 mL) and diluted with ether (500 mL). The layers were separated and the aqueous layer was extracted with ether (2×150 mL). The combined organics were dried over sodium sulfate, filtered and concentrated. The crude product was purified on silica gel eluting with a 0, 10, 15, 75% ethyl acetate in hexanes step gradient to give the title compound.

Workup

  1. stirringAfter stirring for 72 hours
  2. customthe reaction was quenched with saturated aqueous ammonium chloride solution (400 mL)
  3. additiondiluted with ether (500 mL)
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with ether (2×150 mL)
  6. dry with materialThe combined organics were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product was purified on silica gel eluting with a 0, 10, 15, 75% ethyl acetate in hexanes step gradient

Sources & evidence

ORD record
ord-d790d64720be47daa13d8fbea0301a90
Source dataset
uspto-grants-2015_07
Patent number
US09073855B2

Reaction notes

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