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

HRID 2423126노트

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HRID 2423126 반응식
[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]

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 14797Potassium HydroxideHCID 99705131-(Phenylsulfonyl)-1H-indol-5-ol2회

생성물 1

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

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매HCID 6344Dichloromethane용매

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온도
40 °C

실험 절차

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]+.

후처리

  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×)

출처 및 근거

ORD 기록
ord-a29f71793313418abb780e54292f3015
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07960374B2

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