Potassium Sodium Tartrate → HCID 59577402, compound

HRID 1947469Notes

Reaction equation

HRID 1947469 reaction equation
C[O:2][C:3]([C:5]1[O:6][C:7]2[CH:13]=[CH:12][C:11]([O:14][C:15]3[S:16][C:17]4[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=4[N:19]=3)=[CH:10][C:8]=2[CH:9]=1)=O.CC(C[AlH]CC(C)C)C.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+].[NH4+].[Cl-]>C(Cl)Cl>[S:16]1[C:17]2[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=2[N:19]=[C:15]1[O:14][C:11]1[CH:12]=[CH:13][C:7]2[O:6][C:5]([CH2:3][OH:2])=[CH:9][C:8]=2[CH:10]=1

Participants

6

Reactant 4

HCID 9357Potassium Sodium TartrateHCID 14487Diisobutylaluminum hydrideHCID 25517Ammonium ChlorideHCID 66786446HCID 66786446, compound

Product 1

HCID 59577402HCID 59577402, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled (0° C.) solution of 5-(benzothiazol-2-yloxy)-benzofuran-2-carboxylic acid methyl ester (170 mg, 0.52 mmol) in DCM (2 mL) was added DIBALH (0.63 mL, 89 mg 0.63 mmol) and the reaction mixture was warmed (rt, 2.5 h). The reaction mixture was treated with saturated aqueous Rochelle's Salt (2 mL) and stirred (rt, 2 h). The biphasic mixture was poured into saturated aqueous NH4Cl and extracted with DCM (2×50 mL). The organic layer was dried, filtered and concentrated in vacuo. The resultant residue was purified by silica gel flash column chromatography using MeOH:DCM (3-40%) to afford the title compound (55 mg, 36%). MS (ESI): mass calcd for C16H11NO3S, 297.04; m/z found, 298.1 [M+H]+.

Workup

  1. extractionextracted with DCM (2×50 mL)
  2. customThe organic layer was dried
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe resultant residue was purified by silica gel flash column chromatography

Sources & evidence

ORD record
ord-72f7f10d5d52489d8b69cf67a41f94c5
Source dataset
uspto-grants-2013_03
Patent number
US08399465B2

Reaction notes

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