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

HRID 1067855Notes

Reaction equation

HRID 1067855 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-f9a7e8a9ee404df6badf933cc87e02cd
Source dataset
uspto-grants-2001_06
Patent number
US06248781B1

Reaction notes

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