Methanol → HCID 86665800, compound

HRID 1623220Notes

Reaction equation

HRID 1623220 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:11][CH2:12][CH2:13][C:14]2[CH:15]=[C:16]3[C:21](=[CH:22][CH:23]=2)[O:20][CH2:19][CH2:18][C:17]3=[O:24])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[OH-:25].[K+].[C:27](OC1C(OC(=O)C)=C(I)C=CC=1)(=[O:29])C.[CH3:42]O>>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([O:11][CH2:12][CH2:13][C:14]2[CH:15]=[C:16]3[C:21](=[CH:22][CH:23]=2)[O:20][CH2:19][CH:18]([OH:25])[C:17]3([O:29][CH3:27])[O:24][CH3:42])(=[O:10])=[O:9])=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 887Methanol2×HCID 14797Potassium HydroxideHCID 21865429Bis(acetoxy)iodobenzene2×HCID 59318294HCID 59318294, compound

Product 1

HCID 86665800HCID 86665800, compoundYield 76%

Procedure

A suspension of 2-(4-oxo-3,4-dihydro-2H-chromen-6-yl)ethyl 4-methylbenzenesulfonate (RE6) (10.0 g, 29 mmol) in methanol (200 mL) was added to a solution of potassium hydroxide (4.86 g, 87 mmol) in methanol (100 mL) under ice cooling. To the reaction mixture, diacetoxyiodobenzene (10.2 g, 32 mmol) was added in small portions for 5 minutes with the temperature kept at 5° C. or lower, and the reaction mixture was gradually warmed to room temperature and stirred for 1 day. Bisacetoxyiodobenzene (2.00 g, 6.2 mmol) was further added thereto at room temperature, and the mixture was stirred for 3 hours. Then, methanol was distilled off under reduced pressure. Water (100 mL) was added to the obtained concentrated residue, followed by extraction with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. Then, the obtained concentrated residue was suspended by the addition of diethyl ether (50 mL), and the resulting precipitate was collected by filtration, washed with diethyl ether (5 mL×2), and then dried under reduced pressure to obtain the title compound (RE8) (8.99 g, 76%) as a white powder.

Workup

  1. customkept at 5° C.
  2. stirringat room temperature, and the mixture was stirred for 3 hours
  3. distillationThen, methanol was distilled off under reduced pressure
  4. additionWater (100 mL) was added to the obtained concentrated residue
  5. extractionfollowed by extraction with ethyl acetate
  6. washThe organic layer was washed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationThe solvent was distilled off under reduced pressure
  9. additionThen, the obtained concentrated residue was suspended by the addition of diethyl ether (50 mL)
  10. filtrationthe resulting precipitate was collected by filtration
  11. washwashed with diethyl ether (5 mL×2)
  12. customdried under reduced pressure

Sources & evidence

ORD record
ord-13ecfabb96164a2d9ae6d5239ec4a575
Source dataset
uspto-grants-2014_07
Patent number
US08778970B2

Reaction notes

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