Sodium hydride → 2-(5H-dibenzo[a,d]cyclohepten-5-yloxy)-ethanol

HRID 1060843Notes

Reaction equation

HRID 1060843 reaction equation
[CH:1]1[CH:15]=[C:14]2[C:4]([CH:5]([OH:16])[C:6]3[C:11]([CH:12]=[CH:13]2)=[CH:10][CH:9]=[CH:8][CH:7]=3)=[CH:3][CH:2]=1.[H-].[Na+].[C:19]([O:23]C(=O)CBr)(C)(C)[CH3:20].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1.CCOCC>[CH:15]1[C:14]2[CH:13]=[CH:12][C:11]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[CH:5]([O:16][CH2:20][CH2:19][OH:23])[C:4]=2[CH:3]=[CH:2][CH:1]=1

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 82577DibenzosuberenolHCID 21226445Aluminium lithium hydride

Product 1

HCID 100835672-(5H-dibenzo[a,d]cyclohepten-5-yloxy)-ethanolYield 51.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Dibenzosuberenol (2.08 g, 10 mmol) was dissolved in dry THF (20 mL) at 0° C. Sodium hydride (1.0 g of 50% mineral oil dispersion, 20 mmol) was added. After 10 min. tert-butylbromoacetate (4.0 g, 20.0 mmol) was added over a period of 20 min and then stirred for 1 h. The reaction mixture was quenched with water at 0° C. and the product extracted with ethyl acetate. The combined extracts were dried (MgSO4), and concentrated in vacuo. The product was-redissolved in ether (20 mL) and added dropwise to an ether (15 mL) suspension of lithium aluminium hydride (190 mg, 5.0 mmol). The reaction was stirred 16 h at room temperature, quenched with water. The ether solution was washed with water, dried, and concentrated in vacuo to give 1.3 g (50%) of 2-(5H-dibenzo[a,d]cyclohepten-5-yloxy)-ethanol.

Workup

  1. customThe reaction mixture was quenched with water at 0° C.
  2. extractionthe product extracted with ethyl acetate
  3. dry with materialThe combined extracts were dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. dissolutionThe product was-redissolved in ether (20 mL)
  6. stirringThe reaction was stirred 16 h at room temperature
  7. customquenched with water
  8. washThe ether solution was washed with water
  9. customdried
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-63886c0780ae41c7b6dd0604ed9b8d87
Source dataset
uspto-grants-2003_02
Patent number
US06525086B2

Reaction notes

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