HCID 71245549, compound → HCID 71245453, compound

HRID 532128Notes

Reaction equation

HRID 532128 reaction equation
[CH2:1]([Mg]Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:10][O:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[O:18][CH2:17][CH:16]([NH:22][C:23](=[O:27])[O:24][CH2:25][CH3:26])[C:15]2=[O:28]>C1COCC1>[CH2:1]([C:15]1([OH:28])[C:14]2[C:19](=[CH:20][CH:21]=[C:12]([O:11][CH3:10])[CH:13]=2)[O:18][CH2:17][CH:16]1[NH:22][C:23](=[O:27])[O:24][CH2:25][CH3:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 71245549HCID 71245549, compoundHCID 178418336HCID 178418336, compound

Product 1

HCID 71245453HCID 71245453, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

26.4 ml (52.8 mmol) of benzylmagnesium chloride under nitrogen atmosphere were cooled to 0° C. with an ice bath and 3.5 g (13.2 mmol) ethyl 6-methoxy-4-oxochroman-3-ylcarbamate dissolved in 100 ml dry THF were slowly added. The mixture was stirred at 0° C. for 1 h. The cooling bath was removed and saturated ammonium chloride solution was added. Water was added until a clear solution was obtained. The phases were separated and the organic phase was washed with saturated ammonium chloride solution, dried over MgSO4, and concentrated in vacuo to give 6.87 g (9.1 mmol, quant.) of crude material.

Workup

  1. additionwere slowly added
  2. customThe cooling bath was removed
  3. additionsaturated ammonium chloride solution was added
  4. additionWater was added until a clear solution
  5. customwas obtained
  6. customThe phases were separated
  7. washthe organic phase was washed with saturated ammonium chloride solution
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated in vacuo
  10. customto give 6.87 g (9.1 mmol, quant.) of crude material

Sources & evidence

ORD record
ord-ba7ff9363f884c979b9e20af1f9d54da
Source dataset
uspto-grants-2014_10
Patent number
US08853196B2

Reaction notes

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