Ethylene Glycol → 5'-bromo-3',4'-dihydro-1'H-spiro[[1,3]-dioxolane-2,2'-naphthalene]

HRID 1423381노트

반응식

HRID 1423381 반응식
[CH2:1]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6](C=O)[C:5]=2[CH2:4][CH2:3][C:2]21[O:16][CH2:15][CH2:14][O:13]2.[Br:17]C1C=CC=C2C=1CCC(=O)C2.C(O)CO.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1.CCOCC>[Br:17][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:5]=1[CH2:4][CH2:3][C:2]1([O:16][CH2:15][CH2:14][O:13]1)[CH2:1]2

참가 물질

7

반응물 4

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 40596895-Bromo-2-tetraloneHCID 866887243',4'-Dihydro-1'H-spiro[[1,3]dioxolane-2,2'-naphthalene]-5'-carbaldehyde

생성물 1

HCID 866887235'-bromo-3',4'-dihydro-1'H-spiro[[1,3]-dioxolane-2,2'-naphthalene]수율 98%

시약·촉매·용매 2

HCID 241Benzene용매HCID 3283Diethyl Ether용매

실험 절차

3′,4′-Dihydro-1′H-spiro[[1,3]dioxolane-2,2′-naphthalene]-5′-carbaldehyde, designated as 37 in FIG. 15, was prepared as follows: A solution of 5-bromo-3,4-dihydronaphthalen-2(1H)-one (625 mg, 2.78 mmol), ethylene glycol (0.23 mL, 4.17 mmol), and p-toluenesulfonic acid (5.70 mg, 0.03 mol) in benzene (46 mL) was stirred and heated to reflux for 10 h. The solution was cooled, diluted with ether, and sequentially washed with saturated aqueous sodium bicarbonate solution and water. The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo. Purification by silica gel column chromatography, using a 2:1 mixture of hexanes and AcOEt as eluant, furnished 5′-bromo-3′,4′-dihydro-1′H-spiro[[1,3]-dioxolane-2,2′-naphthalene](730.4 mg, 98% yield) as a yellow oil. Yield: 65%.

후처리

  1. customwas prepared
  2. temperatureheated
  3. temperatureto reflux for 10 h
  4. temperatureThe solution was cooled
  5. washsequentially washed with saturated aqueous sodium bicarbonate solution and water
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customPurification by silica gel column chromatography
  10. additiona 2:1 mixture of hexanes and AcOEt as eluant

출처 및 근거

ORD 기록
ord-cb4ce1ff52c44fddbe565c998b020cf8
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08927586B2

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