Acetic Acid → HCID 178489653, compound

HRID 1471883

Reaction equation

HRID 1471883 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=O)[CH:6]=[CH:7][CH:8]=1.CC(C)([O-])C.[K+].[C:24](=[S:26])=S.Br[CH2:28][CH2:29][O:30][CH:31]1[CH2:36][CH2:35][CH2:34][CH2:33][O:32]1.C(O)(=O)C.O.[NH2:42][NH2:43]>C1COCC1.C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[N:42][NH:43][C:24]=2[S:26][CH2:28][CH2:29][O:30][CH:31]2[CH2:36][CH2:35][CH2:34][CH2:33][O:32]2)[CH:6]=[CH:7][CH:8]=1

Participants

9

Reactant 6

HCID 176Acetic AcidHCID 6348Carbon DisulfideHCID 24654Hydrazine hydrate (1:1)HCID 866212-(2-Bromoethoxy)tetrahydro-2H-pyranHCID 27596142-(3-Methoxyphenyl)-1-phenylethan-1-oneHCID 23665647Potassium tert-butoxide

Product 1

HCID 178489653HCID 178489653, compoundYield 74.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2-(3-methoxyphenyl)-1-phenylethanone (1.25 g, 5.52 mmol) in THF (11.05 mL) was added potassium tert-butoxide (11.49 mL, 11.49 mmol). After 30 min, CS2 (0.363 mL, 6.02 mmol) was added and the mixture was stirred for 10 min before 2-(2-bromoethoxy)tetrahydro-2H-pyran (2.086 mL, 13.81 mmol) was added and the reaction was stirred overnight. The mixture was diluted with ethanol (11.05 mL). Acetic acid (1.898 mL, 33.1 mmol) was added followed by hydrazine hydrate (2.71 mL, 55.2 mmol). The reaction was stirred at 85° C. overnight and concentrated under reduced pressure. The residue was extracted with EtOAc/H2O (twice). The organic phases were combined and washed with brine, dried over MgSO4 and concentrated. The residue was purified by silica gel column chromatography to give the title compound as a white solid (1.681 g). 1H NMR (400 MHz, CDCl3) δ ppm 1.52-1.64 (m, 3H), 1.65-1.93 (m, 3H), 3.06 (t, J=5.94 Hz, 2H), 3.49-3.57 (m, 1H), 3.65-3.71 (m, 1H), 3.72 (s, 3H), 3.88-3.95 (m, 1H), 3.97-4.05 (m, 1H), 4.66-4.69 (m, 1H), 6.79-6.90 (m, 3H), 7.19-7.26 (m, 1H), 7.26-7.33 (m, 3H), 7.37-7.45 (m, 2H), 10.91 (bs, 1H).

Workup

  1. additionwas added
  2. stirringThe reaction was stirred at 85° C. overnight
  3. concentrationconcentrated under reduced pressure
  4. extractionThe residue was extracted with EtOAc/H2O (twice)
  5. washwashed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-2eb3ade9b8fa4674a7a9e4d78e88bc0e
Source dataset
uspto-grants-2015_04
Patent number
US09012478B2

Linked notes

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