Sodium hydride → 2-(6,11-Dihydrodibenzo[b,e]oxepin-11-yloxy)-ethanol

HRID 394632Notes

Reaction equation

HRID 394632 reaction equation
[CH:1]1[C:11]2[CH:10]([OH:12])[C:9]3[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=3[CH2:7][O:6][C:5]=2[CH:4]=[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:1]1[C:11]2[CH:10]([O:12][CH2:20][CH2:19][OH:23])[C:9]3[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=3[CH2:7][O:6][C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 21226445Aluminium lithium hydrideHCID 22727883HCID 22727883, compound

Product 1

HCID 227276792-(6,11-Dihydrodibenzo[b,e]oxepin-11-yloxy)-ethanolYield 21%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
35 °C

Procedure

6,11-Dihydrodibenzo[b,e]oxepin-11-ol (1.06 g, 5 mmol) was dissolved in dry THF (25 mL) at 0° C. Sodium hydride (0.24 g of 50% mineral oil dispersion, 5 mmol) was added portionwise at 0° C. and then refluxed for 30 min. tert-Butylbromoacetate (980 mg, 5.0 mmol) in dry THF (10 mL) was added over a period of 20 and the mixture stirred at 35° C. for 16 h. The reaction mixture was quenched with water at 0° C. and the product extracted with ether. The combined extracts were dried (MgSO4), and concentrated in vacuo. The, product was redissolved in ether and added dropwise to an ether (15 mL) suspension of lithium aluminium hydride (190 mg, 5.0 mmol). The reaction was stirred 48 h at room temperature, quenched with water, cooled, and filtered through Decalit. The ether solution was washed with saturated NaCl, dried, and purified by chromatography eluting with ethyl acetate/dichloromethan (1:10) to give 267 mg (21%) of 2-(6,11-dihydrodibenzo[b,e]oxepin-11-yloxy)-ethanol.

Workup

  1. customThe reaction mixture was quenched with water at 0° C.
  2. extractionthe product extracted with ether
  3. dry with materialThe combined extracts were dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. dissolutionThe, product was redissolved in ether
  6. stirringThe reaction was stirred 48 h at room temperature
  7. customquenched with water
  8. temperaturecooled
  9. filtrationfiltered through Decalit
  10. washThe ether solution was washed with saturated NaCl
  11. customdried
  12. custompurified by chromatography
  13. washeluting with ethyl acetate/dichloromethan (1:10)

Sources & evidence

ORD record
ord-55bf5ddd11d2452da2f68563f7f987e1
Source dataset
uspto-grants-2003_08
Patent number
US06602901B2

Reaction notes

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