Water → 5,8-Dimethoxy-1,2,3,4-tetrahydro-2-hydroxy-2-naphthaleneethanol

HRID 2118764ノート

反応式

HRID 2118764 の反応式
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[C:9]2[C:4]=1[CH2:5][CH2:6][C:7]([OH:19])([CH2:15][C:16](O)=[O:17])[CH2:8]2.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)(=O)C.O>O1CCCC1>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[C:9]2[C:4]=1[CH2:5][CH2:6][C:7]([OH:19])([CH2:15][CH2:16][OH:17])[CH2:8]2

参加物

6

反応物 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 201931955,8-Dimethoxy-1,2,3,4-tetrahydro-2-hydroxy-2-naphthaleneacetic acidHCID 21226445Aluminium lithium hydride

生成物 1

HCID 201932595,8-Dimethoxy-1,2,3,4-tetrahydro-2-hydroxy-2-naphthaleneethanol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

15.5 g of 5,8-dimethoxy-1,2,3,4-tetrahydro-2-hydroxy-2-naphthaleneacetic acid in 150 ml of tetrahydrofuran were added dropwise within 15 minutes to 3.32 g of lithium aluminum hydride in 150 ml of tetrahydrofuran. The reaction mixture was heated to reflux for 1 hour and then cooled. After the dropwise addition of 15 ml of ethyl acetate and 20 ml of water the suspension was filtered and the filtrate was concentrated. The product was purified by column chromatography (silica gel, chloroform/methanol 30:1). There was obtained 5,8-dimethoxy-1,2,3,4-tetrahydro-2-hydroxy-2-naphthaleneethanol, m.p. 121°-122°.

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 1 hour
  3. temperaturecooled
  4. filtrationwas filtered
  5. concentrationthe filtrate was concentrated
  6. customThe product was purified by column chromatography (silica gel, chloroform/methanol 30:1)

出典と根拠

ORDレコード
ord-e5c5f0ec6ca846a98812021bed316aab
出典データセット
uspto-grants-1987_07
特許番号
US04680310

反応ノート

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