Methanol → 7-Methoxy-1,2,3,4-tetrahydronaphthalen-2-ol

HRID 643901

反応式

HRID 643901 の反応式
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH2:9][CH2:10]2)=[CH:5][CH:4]=1.[BH4-].[Na+].[NH4+].[Cl-].C[OH:18]>>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH:9]([OH:18])[CH2:10]2)=[CH:5][CH:4]=1

参加物

5

反応物 4

HCID 887Methanol2 回HCID 25517Ammonium ChlorideHCID 744146-MethoxytetralinHCID 4311764Sodium borohydride

生成物 1

HCID 230252467-Methoxy-1,2,3,4-tetrahydronaphthalen-2-ol

反応条件

温度
-20 °C

実験手順

A solution of 7-methoxy-3,4-dihydro-1H-naphthalene (5.00 g, 28.4 mmol) in MeOH (5 mL) is added to a suspension of NaBH4 (2.8 g, 74 mmol) in MeOH (40 mL) at −20° C. The mixture is stirred at −20° C. for 10 min. Solid NH4Cl is added, and the mixture is concentrated to remove most of the MeOH. The residue is partitioned between EtOAc and, sequentially, aq. NH4Cl and brine. The organic layer is dried over MgSO4 and concentrated to afford 7-methoxy-1,2,3,4-tetrahydronaphthalen-2-ol as a red solid.

後処理

  1. concentrationthe mixture is concentrated
  2. customto remove most of the MeOH
  3. customThe residue is partitioned between EtOAc
  4. dry with materialThe organic layer is dried over MgSO4
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-b0fdc90f0edb422d89e00836ca254aa7
出典データセット
uspto-grants-2010_04
特許番号
US07700633B2

関連ノート

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