Hydrochloric Acid → 4-(Hydroxymethyl)-1-(phenylsulfonyl)-1H-indol-5-ol

HRID 2423126ノート

反応式

HRID 2423126 の反応式
[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][C:15]([OH:19])=[CH:16][CH:17]=3)[CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:20]=[O:21].[OH-].[K+].Cl>CO.O.C(Cl)Cl>[OH:21][CH2:20][C:14]1[C:15]([OH:19])=[CH:16][CH:17]=[C:18]2[C:13]=1[CH:12]=[CH:11][N:10]2[S:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)(=[O:8])=[O:9]

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 14797Potassium HydroxideHCID 99705131-(Phenylsulfonyl)-1H-indol-5-ol2 回

生成物 1

HCID 672416334-(Hydroxymethyl)-1-(phenylsulfonyl)-1H-indol-5-ol収率 48.9%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
40 °C

実験手順

1-(Phenylsulfonyl)-1H-indol-5-ol (Intermediate 8, 0.80 g, 2.9 mmol) was dissolved in MeOH (20 mL) and formaldehyde (37 wt. % in H2O, 4.0 mL, 49 mmol) was added followed by a solution of KOH (1.64 g, 29.3 mmol) in water (20 mL). The reaction mixture was heated at 40° C. overnight. The mixture was made acidic with 1 M HCl and diluted with DCM, transferred to a separation funnel and extracted with DCM (2×). The combined organics were washed with brine (1×), dried (MgSO4) and evaporated. The crude product was dissolved in diethylether (100 mL) and evaporated to approximately 20 mL (precipitation of white crystals). The white crystals were filtered and washed with diethylether (2×) to give 0.43 g of the title compound as a white solid. MS m/z 286 [M+H—H2O]+.

後処理

  1. customtransferred to a separation funnel
  2. extractionextracted with DCM (2×)
  3. washThe combined organics were washed with brine (1×)
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. dissolutionThe crude product was dissolved in diethylether (100 mL)
  7. customevaporated to approximately 20 mL (precipitation of white crystals)
  8. filtrationThe white crystals were filtered
  9. washwashed with diethylether (2×)

出典と根拠

ORDレコード
ord-a29f71793313418abb780e54292f3015
出典データセット
uspto-grants-2011_06
特許番号
US07960374B2

反応ノート

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