Methanol → [1-(2,4,6-Trimethyl-benzenesulfonyl)-1H-pyrrol-2-yl]-methanol

HRID 2181551ノート

反応式

HRID 2181551 の反応式
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[S:10]([N:13]1[CH:17]=[CH:16][CH:15]=[C:14]1[CH:18]=[O:19])(=[O:12])=[O:11].[Li+].[BH4-].CO>C1COCC1.[Cl-].[Na+].O>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[S:10]([N:13]1[CH:17]=[CH:16][CH:15]=[C:14]1[CH2:18][OH:19])(=[O:12])=[O:11]

参加物

6

反応物 3

HCID 887MethanolHCID 4148881Lithium borohydrideHCID 218774321-(2,4,6-Trimethyl-benzenesulfonyl)-1H-pyrrole-2-carbaldehyde

生成物 1

HCID 21877558[1-(2,4,6-Trimethyl-benzenesulfonyl)-1H-pyrrol-2-yl]-methanol収率 87%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

1-(2,4,6-Trimethyl-benzenesulfonyl)-1H-pyrrole-2-carbaldehyde (2.77 g, 10 mmol) in THF (0.100 ml) was treated with LiBH4 (0.44 g, 20 mmol) at rt. The resulting solution was held at rt for 1 h. MeOH (10 ml) was then added, and the resulting mixture mixture was poured into brine (600 ml), and extracted with EtOAc (3×200 ml). The combined organic layer was dried over MgSO4 and concentrated under reduced pressure. The resulting oil was then purified on silica gel column to yield [1-(2,4,6-Trimethyl-benzenesulfonyl)-1H-pyrrol-2-yl]-methanol as a light brown oil (2.43 g, 87%). 1H NMR (CDCl3) δ 7.17 (dd, 1H, J=3.3, 1.8 Hz), 6.99 (s, 2H), 6.28-6.23 (m, 1H), 6.18 (t, 1H, J=3.3 Hz), 4.42 (s, 2H), 2.50 (s, 6H), 2.30 (s, 3H).

後処理

  1. extractionextracted with EtOAc (3×200 ml)
  2. dry with materialThe combined organic layer was dried over MgSO4
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting oil was then purified on silica gel column

出典と根拠

ORDレコード
ord-9e88414996bd4e75ac91203c05adc62b
出典データセット
uspto-grants-2005_05
特許番号
US06891044B2

反応ノート

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