Benzyl Bromide → 8-[2-(Benzyloxy)ethyl]-1,4-dioxaspiro[4.5]decane

HRID 1486210Notes

Reaction equation

HRID 1486210 reaction equation
[H-].[Na+].[O:3]1[C:7]2([CH2:12][CH2:11][CH:10]([CH2:13][CH2:14][OH:15])[CH2:9][CH2:8]2)[O:6][CH2:5][CH2:4]1.[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C1COCC1>[CH2:16]([O:15][CH2:14][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:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 118054582-(1,4-Dioxaspiro(4.5)decan-8-yl)ethan-1-ol

Product 1

HCID 218796038-[2-(Benzyloxy)ethyl]-1,4-dioxaspiro[4.5]decaneYield 83.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a precooled (0° C.) suspension of NaH (60% in mineral, 0.44 g, 11 mmol) in THF (20 mL) was added 2-(1,4-dioxaspiro[4.5]decan-8-yl)ethanol (1.86 g, 10 mmol) in THF (10 mL). The resulting solution was stirred at 0° C. for 10 min, and allowed to warm to RT, and stirred for 1 h. To the above mixture was added benzyl bromide (1.78 g, 15 mmol) and the resulting mixture was stirred at rt overnight. The reaction was quenched by addition of saturated aqueous NH4Cl solution, extracted with EtOAc, washed with brine, dried over Na2SO4. Purification by flash column chromatography (eluent: 20% EtOAc in hexanes to 30%) gave the product (2.3 g, 83%). LC/MC: 277.1 (MH)+.

Workup

  1. temperatureto warm to RT
  2. stirringstirred for 1 h
  3. stirringthe resulting mixture was stirred at rt overnight
  4. customThe reaction was quenched by addition of saturated aqueous NH4Cl solution
  5. extractionextracted with EtOAc
  6. washwashed with brine
  7. dry with materialdried over Na2SO4
  8. customPurification by flash column chromatography (eluent: 20% EtOAc in hexanes to 30%)

Sources & evidence

ORD record
ord-8205fa951cf04e36a54e3417a9f69ec7
Source dataset
uspto-grants-2016_08
Patent number
US09422314B2

Reaction notes

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