Methanol → HCID 17821171、化合物

HRID 1169169ノート

反応式

HRID 1169169 の反応式
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:12]=2[CH2:13][CH2:14][C:15]3=O)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+].CO.[Cl-].[NH4+]>C1(C)C=CC=CC=1>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:12]=2[CH:13]=[CH:14][CH2:15]3)=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

参加物

6

反応物 4

HCID 887MethanolHCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 229905194-(4-tert-Butyl-phenyl)-indan-1-one

生成物 1

HCID 17821171HCID 17821171、化合物収率 86.4%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
50 °C

実験手順

9.0 g (34 mmol) of 4-(4′-tert-butylphenyl)indanone and 1.3 g (34 mmol) of sodium borohydride together with 32 ml of toluene are placed in a reaction vessel. The reaction mixture is heated to 50° C., after which 6.2 ml (148 mmol) of methanol are added over a period of 10 minutes. After the addition is complete, the mixture is stirred at 50° C. for 2 hours. After addition of 30 ml of a saturated ammonium chloride solution, the mixture is stirred for another 30 minutes. After separating off the aqueous phase, the organic phase is washed once with a saturated ammonium chloride solution and once with a saturated sodium chloride solution. After drying over magnesium sulfate, the solvent mixture is removed on a rotary evaporator, the residue is made up to a total volume of 150 ml with toluene and is admixed with 0.2 g of p-toluenesulfonic acid. After 30 minutes, no more elimination of water is observed. The reaction mixture is subsequently washed once with a saturated sodium hydrogen carbonate solution, then dried over magnesium sulfate and the solvent is removed in an oil pump vacuum. 7.3 g (86%) of the desired product are isolated.

後処理

  1. additionAfter the addition
  2. stirringthe mixture is stirred for another 30 minutes
  3. customAfter separating off the aqueous phase
  4. washthe organic phase is washed once with a saturated ammonium chloride solution and once with a saturated sodium chloride solution
  5. dry with materialAfter drying over magnesium sulfate
  6. customthe solvent mixture is removed on a rotary evaporator
  7. waitAfter 30 minutes
  8. washThe reaction mixture is subsequently washed once with a saturated sodium hydrogen carbonate solution
  9. dry with materialdried over magnesium sulfate
  10. customthe solvent is removed in an oil pump vacuum

出典と根拠

ORDレコード
ord-ce94f439f2de4510ac7e59c2d5984922
出典データセット
uspto-grants-2003_09
特許番号
US06627764B1

反応ノート

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