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

HRID 1423381ノート

反応式

HRID 1423381 の反応式
[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

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 241Benzene溶媒HCID 3283Diethyl Ether溶媒

実験手順

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%.

後処理

  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

出典と根拠

ORDレコード
ord-cb4ce1ff52c44fddbe565c998b020cf8
出典データセット
uspto-grants-2015_01
特許番号
US08927586B2

反応ノート

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