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

HRID 394627노트

반응식

HRID 394627 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-0cafe3a455dc4b14bff9aaf87c353ac3
출처 데이터셋
uspto-grants-2003_08
특허 번호
US06602901B2

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