Hydrochloric Acid → HCID 178497301, compound

HRID 1507455Notes

Reaction equation

HRID 1507455 reaction equation
[OH:1][C:2]1[C:7]([CH3:8])=[C:6]([O:9][CH2:10][O:11][CH3:12])[CH:5]=[CH:4][C:3]=1[C:13](=[O:16])[CH2:14][CH3:15].[C:17](=[S:19])=S.CC(C)([O-])C.[K+].Cl>O1CCCC1.O>[OH:16][C:13]1[C:3]2[C:2](=[C:7]([CH3:8])[C:6]([O:9][CH2:10][O:11][CH3:12])=[CH:5][CH:4]=2)[O:1][C:17](=[S:19])[C:14]=1[CH3:15]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6348Carbon DisulfideHCID 23665647Potassium tert-butoxideHCID 117701621HCID 117701621, compound

Product 1

HCID 178497301HCID 178497301, compoundYield 80.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

According to the method described in Eur. J. Med. Chem. 36 (2001) 697, a solution of 1-[2-hydroxy-4-(methoxymethoxy)-3-methylphenyl]propan-1-one (3.99 g, 17.8 mmol) obtained in Example 2-1 and carbon disulfide (1.07 mL, 17.8 mmol) in tetrahydrofuran (30 mL) was added to a solution of potassium t-butoxide (5.99 g, 53.4 mmol) in tetrahydrofuran (20 mL), and the mixture was stirred overnight at room temperature. Water (50 mL) was added to the reaction solution, and then the pH of the mixture was adjusted to 5 with 2 M hydrochloric acid, followed by extraction with ethyl acetate. The pH of the aqueous layer was adjusted to 5 again with 2 M hydrochloric acid, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine and then dried over magnesium sulfate. The solvent was concentrated under reduced pressure to obtain 3.80 g of the title compound (yield: 80%).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationThe solvent was concentrated under reduced pressure

Sources & evidence

ORD record
ord-6bd36fa23ca34565be2341209c244171
Source dataset
uspto-grants-2015_12
Patent number
US09221811B2

Reaction notes

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