Methyl 2,3-dihydrobenzofuran-7-carboxylate → HCID 66893378, compound

HRID 1162070Notes

Reaction equation

HRID 1162070 reaction equation
[O:1]1[C:5]2[C:6]([C:10]([O:12][CH3:13])=[O:11])=[CH:7][CH:8]=[CH:9][C:4]=2[CH2:3][CH2:2]1.[CH3:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][C:17]=1[S:23](O)(=[O:25])=[O:24].O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.CS(O)(=O)=O>>[CH3:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][C:17]=1[S:23]([C:8]1[CH:7]=[C:6]([C:10]([O:12][CH3:13])=[O:11])[C:5]2[O:1][CH2:2][CH2:3][C:4]=2[CH:9]=1)(=[O:24])=[O:25]

Participants

4

Reactant 3

HCID 15062252Methyl 2,3-dihydrobenzofuran-7-carboxylate2×HCID 21032527HCID 21032527, compound2×HCID 86584057Phosphorus Pentoxide-Methanesulfonic Acid

Product 1

HCID 66893378HCID 66893378, compound

Procedure

To methyl 2,3-dihydro-1-benzofuran-7-carboxylate (1 g, 5.6 mmol; Intermediate 65) were 2-methoxy-5-methylbenzenesulfonic acid (1.13 g, 5.6 mmol) and phosphorus pentoxide-methanesulfonic acid solution (1:10; 13.5 mL) added. The mixture was stirred at room temperature for 48 h. Additional 2-methoxy-5-methylbenzenesulfonic acid (0.56 g, 2.8 mmol) was added and the reaction mixture was stirred at 50° C. for 15 h. The mixture was poured onto water/ice and the formed precipitate was filtrated off, dissolved in DCM and evaporated. The crude product was purified using flash chromatography (eluent: isohexane:EtOAc 1:1) yielding the title compound. Yield: 1.07 g (53%). MS (ESI+) for C18H18O6S m/z 363 (M+H)+.

Workup

  1. additionadded
  2. stirringthe reaction mixture was stirred at 50° C. for 15 h
  3. additionThe mixture was poured onto water/ice
  4. filtrationthe formed precipitate was filtrated off
  5. dissolutiondissolved in DCM
  6. customevaporated
  7. customThe crude product was purified

Sources & evidence

ORD record
ord-6b63885fc83146d78bde23bf787892a4
Source dataset
uspto-grants-2010_10
Patent number
US07820675B2

Reaction notes

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