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

HRID 2423126Notes

Reaction equation

[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]

Participants

Conditions

Temperature: 40 °C

Procedure

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]+.

Workup

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

Sources & evidence

ORD record: ord-a29f71793313418abb780e54292f3015
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07960374B2

Reaction notes

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