Hydrochloric Acid → HCID 13560307, compound

HRID 637732Notes

Reaction equation

C(O)(=O)C.C([O:8][C:9]1[C:10]([CH2:19]O)=[CH:11][C:12]2[O:17][CH2:16][CH2:15][CH2:14][C:13]=2[CH:18]=1)(=O)C.[C:21]([C:24]1[CH:30]=[CH:29][C:27]([S-:28])=[CH:26][CH:25]=1)(=[O:23])[CH3:22].[K+].[OH-].[Na+].Cl>CN(C)C=O>[OH:8][C:9]1[C:10]([CH2:19][S:28][C:27]2[CH:29]=[CH:30][C:24]([C:21](=[O:23])[CH3:22])=[CH:25][CH:26]=2)=[CH:11][C:12]2[O:17][CH2:16][CH2:15][CH2:14][C:13]=2[CH:18]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 6-acetoxy-7-hydroxymethyl-3,4-dihydrobenzopyran acetate (1.00 g, 3.78 mmol) in dry dimethylformamide (5 mL) was added a solution of potassium p-acetylthiophenoxide (720 mg, 3.8 mmol) in dimethylformamide (5 mL). The mixture was heated at 50° C. for 2.25 hours, then poured into ice water (75 mL). Sodium hydroxide (10% aqueous, 20 mL) was added, then mixture allowed to stir for 30 minutes, then acidified with 2N hydrochloric acid and extracted with ethyl acetate (3×50 mL). The combined extracts were washed with 7% NaHCO3, and brine (2x), dried (Na2SO4) and concentrated. The crude product was purified by preparative HPLC (30% ethyl acetate hexane as eluant and recrystallized from ethyl acetate hexane to afford 6-hydroxy-7-(4-acetylphenyl)thiomethyl-3, 4-dihydrobenzopyran as a white solid (172 mg), m.p. 192°-193° C.

Workup

extractionextracted with ethyl acetate (3×50 mL)
washThe combined extracts were washed with 7% NaHCO3, and brine (2x)
dry with materialdried (Na2SO4)
concentrationconcentrated
customThe crude product was purified by preparative HPLC (30% ethyl acetate hexane as eluant
customrecrystallized from ethyl acetate hexane

Sources & evidence

ORD record: ord-119d04ce60b04be1b705961c62fcada4
Source dataset: uspto-grants-1985_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04558067

Reaction notes

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