Carbon Dioxide → HCID 22640344, compound

HRID 2415113Notes

Reaction equation

HRID 2415113 reaction equation
Br[C:2]1[C:11]2[C:6](=[C:7]([O:17][CH3:18])[CH:8]=[C:9]([CH:12]3OCC[O:13]3)[CH:10]=2)[O:5][C:4]([CH3:20])([CH3:19])[CH:3]=1.C(=O)=O.C([Li])CCC.S([Cl:33])(C)(=O)=O>C1COCC1>[Cl:33][C:2]1[C:11]2[C:6](=[C:7]([O:17][CH3:18])[CH:8]=[C:9]([CH:12]=[O:13])[CH:10]=2)[O:5][C:4]([CH3:20])([CH3:19])[CH:3]=1

Participants

6

Reactant 4

HCID 280Carbon Dioxide2×HCID 31297Methanesulfonyl chlorideHCID 22640375HCID 22640375, compoundHCID 178418339Butyllithium

Product 1

HCID 22640344HCID 22640344, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

366 mg of 4-bromo-6-[1,3]dioxolan-2-yl-8-methoxy-2,2-dimethyl-2H-chromene (1.07 mmol) was dissolved in 4 ml of abs. THF and treated at −78° (dry-ice bath) with 0.735 ml n-butyl lithium (1.6M, n-hexane, 1.1 eq.). 15 min. later, 0.114 ml of mesyl chloride (1.1 eq.) was added and the dry-ice bath replaced by an ice-bth. After 30 min. the reaction mixture was poured onto crushed ice/concentrated HCl and vigorously stirred to cleave the acetal. Twofold extraction with ether, washing with NaCl, drying over magnesium sulfate, and evaporation of the solvents left a crude product which was purified by flash chromatography (SiO2 with n-hexane/AcOEt=87/13) to yield 77 mg of the title compound as white crystals.

Workup

  1. additionAfter 30 min. the reaction mixture was poured
  2. customonto crushed ice/concentrated HCl
  3. extractionextraction with ether
  4. washwashing with NaCl
  5. dry with materialdrying over magnesium sulfate, and evaporation of the solvents
  6. waitleft a crude product which
  7. customwas purified by flash chromatography (SiO2 with n-hexane/AcOEt=87/13)

Sources & evidence

ORD record
ord-2ce97adcbdb84d219642f9aa3e26258b
Source dataset
uspto-grants-2004_11
Patent number
US06818649B2

Reaction notes

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