Hydrochloric Acid → HCID 22602997, compound

HRID 2307933Notes

Reaction equation

HRID 2307933 reaction equation
[CH3:1][C:2]1([CH3:24])[C:11]2[C:6](=[CH:7][C:8]([CH3:23])=[C:9]([CH2:13][C:14]3[O:18][C:17]([C:19]([O:21]C)=[O:20])=[CH:16][CH:15]=3)[C:10]=2[CH3:12])[O:5][CH2:4][CH2:3]1.CO.Cl>O>[CH3:1][C:2]1([CH3:24])[C:11]2[C:6](=[CH:7][C:8]([CH3:23])=[C:9]([CH2:13][C:14]3[O:18][C:17]([C:19]([OH:21])=[O:20])=[CH:16][CH:15]=3)[C:10]=2[CH3:12])[O:5][CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 22603007HCID 22603007, compound

Product 1

HCID 22602997HCID 22602997, compoundYield 67.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a 100-mL round-bottom flask, methyl 5-[(4,4,5,7-tetramethyl-3,4-dihydro-2H-chromen-6-yl)methyl]-2-furoate (532 mg, 1.62 mmol) and methanol (5 mL) were placed. The reaction was stirred at room temperature overnight, and then the mixture was poured in water, acidified with HCl (6N) and extracted with ethyl acetate. The separated organic layer was washed with brine, dried over MgSO4, and concentrated to yield 5-[(4,4,5,7-tetramethyl-3,4-dihydro-2H-chromen-6-yl)methyl]-2-furoic acid (208) (343.6 mg, 67.5% yield). 1HNMR (CDCl3) δ 1.31 (s, 6H), 1.82 (m, 2H), 2.13 (s, 3H), 2.21 (s, 3H), 2.62 (t, 2H), 4.01 (s, 2H), 5.82 (d, 1H), 6.55 (s, 1H), 7.16 (d, 1H). APCI-MS m/z 315 (M+1).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe separated organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b38d57fe69e1471ea29943de9657a7e0
Source dataset
uspto-grants-2004_12
Patent number
US06833372B2

Reaction notes

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