Sodium Carbonate → HCID 59816133, compound

HRID 732301Notes

Reaction equation

HRID 732301 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH2:9][C@@H:8]([CH3:10])[CH2:7][C:6]=1OS(C(F)(F)F)(=O)=O)=[O:4].[CH3:19][O:20][CH2:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][CH2:30][O:31][CH3:32])=[CH:25][C:24]=1B(O)O.[Li+].[Cl-].C([O-])([O-])=O.[Na+].[Na+]>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][O:2][C:3]([C:5]1[CH2:9][C@@H:8]([CH3:10])[CH2:7][C:6]=1[C:25]1[CH:24]=[C:23]([O:22][CH2:21][O:20][CH3:19])[CH:28]=[CH:27][C:26]=1[O:29][CH2:30][O:31][CH3:32])=[O:4]

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 433294Lithium ChlorideHCID 59816159HCID 59816159, compoundHCID 59816160HCID 59816160, compound

Product 1

HCID 59816133HCID 59816133, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

Prepare a mixture of 4-Methyl-2-trifluoromethanesulfonyloxy-cyclopent-1-enecarboxylic acid methyl ester 3a (2.5 g, 8.7 mmol), 2,5-Bis-methoxymethoxy phenylboronic acid 7 (2.31 g, 9.5 mmol), tetrakis(triphenylphosphine)palladium (485 mg, 0.435 mmol), and LiCl (1.1 g, 26.1 mmol) in DME (80 mL). Add 2.0 M solution of Na2CO3 (10 mL, 21.7 mmol) and heat the reaction to reflux and stir for 2 hours. Cool the reaction to room temperature and partitioned between CH2Cl2 and saturated aqueous NaHCO3. Separate and extract the aqueous solution with CH2Cl2 (2×). Combine the organic extracts, dry (Na2SO4), filter and concentrate in vacuo. Purify by flash chromatography (125 g SiO2, 0-30% EtOAc/hexane and 30% EtOAc/hexane) to afford 2-(2,5-Bis-methoxymethoxy-phenyl)-4-methyl-cyclopent-1-enecarboxylic acid methyl ester 8a (2.4 g, 7.1 mmol, 83%) as a yellow oil. 1H NMR (δ, 400 MHz, CDCl3): 7.02 (d, 1H, J=9.2 Hz), 6.90 (dd, 1H, J=9.2, 3.1 Hz), 6.80 (d, 1H, J=3.1 Hz), 5.10 (s, 2H), 5.03 (s, 2H), 3.56 (s, 3H), 3.48 (s, 3H), 3.44 (s, 3H), 3.01-2.91 (m, 2H), 2.53-2.37 (m, 3H), 1.14 (d, 3H, J=6.6 Hz). HRMS calcd. 337.1651; found (electrospray, M+1) 337.1647.

Workup

  1. customPrepare
  2. temperatureheat
  3. customthe reaction
  4. temperatureto reflux
  5. temperatureCool
  6. customthe reaction to room temperature
  7. custompartitioned between CH2Cl2 and saturated aqueous NaHCO3
  8. customSeparate
  9. extractionextract the aqueous solution with CH2Cl2 (2×)
  10. dry with materialCombine the organic extracts, dry (Na2SO4)
  11. filtrationfilter
  12. concentrationconcentrate in vacuo
  13. customPurify by flash chromatography (125 g SiO2, 0-30% EtOAc/hexane and 30% EtOAc/hexane)

Sources & evidence

ORD record
ord-f7249b2b269143008ae5a8095caae89a
Source dataset
uspto-grants-2009_09
Patent number
US07585985B2

Reaction notes

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