Bromine → 6-(Benzyloxy)-2-bromo-1,2,3,4-tetrahydronaphthalen-1-ol

HRID 1433923ノート

反応式

HRID 1433923 の反応式
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[C:15](=[O:19])[CH2:14][CH2:13][CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:20]Br>C(OCC)C>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16]([CH:15]=[C:14]([Br:20])[CH2:13][CH2:12]2)=[CH:17][CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH:15]([OH:19])[CH:14]([Br:20])[CH2:13][CH2:12]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 2

HCID 24408BromineHCID 106822416-(benzyloxy)-3,4-dihydronaphthalen-1(2H)-one

生成物 2

HCID 230872486-(Benzyloxy)-2-bromo-1,2,3,4-tetrahydronaphthalen-1-olHCID 230874203-Bromo-1,2-dihydro-7-(phenylmethoxy)naphthalene

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

The title compound was synthesized by referring to J. Org. Chem., 1984, 49 (22), 4226. To a suspension of 6-benzyloxy-3,4-dihydro-2H-naphthalen-1-one (200 g) in diethyl ether (2 1) was added dropwise bromine (60 ml) on an ice bath, and the solution was stirred overnight at room temperature. The reaction mixture was poured into ice water, extracted with diethyl ether, then sequentially washed with a saturated aqueous solution of sodium bicarbonate, water and brine, dried over anhydrous magnesium sulfate, then filtered through NH silica gel, the solvent was evaporated in vacuo. To the resulting 6-benzyloxy-2-bromo-3,4-dihydro-2H-naphthalen-1-one (250 g) was added ethanol (2.5 1), the solution was stirred, sodium borohydride (25 g) was added thereto on an ice bath followed by stirring overnight at room temperature. The reaction mixture was poured into ice water, and the resulting solid was washed with water to provide 6-benzyloxy-2-bromo-1,2,3,4-tetrahydronaphthalen-1-ol (290 g). To a suspension of this compound (260 g) in toluene (800 ml) was added p-toluenesulfonic acid monohydrate (6.0 g), and the solution was refluxed for 2 hours. The reaction mixture was poured into ice water, extracted with ethyl acetate, then sequentially washed with water and brine, dried over anhydrous magnesium sulfate, then filtered through NH silica gel, and the solvent was evaporated in vacuo. The residue was purified by NH silica gel column chromatography (hexane-ethyl acetate system) to provide the title compound (34 g).

後処理

  1. extractionextracted with diethyl ether
  2. washsequentially washed with a saturated aqueous solution of sodium bicarbonate, water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered through NH silica gel
  5. customthe solvent was evaporated in vacuo
  6. additionTo the resulting 6-benzyloxy-2-bromo-3,4-dihydro-2H-naphthalen-1-one (250 g) was added ethanol (2.5 1)
  7. stirringthe solution was stirred
  8. additionsodium borohydride (25 g) was added
  9. customon an ice bath followed
  10. stirringby stirring overnight at room temperature
  11. additionThe reaction mixture was poured into ice water
  12. washthe resulting solid was washed with water

出典と根拠

ORDレコード
ord-9ec9016982e446ccbe58381033f41432
出典データセット
uspto-grants-2009_11
特許番号
US07612114B2

反応ノート

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