Pivaloyl chloride → HCID 21051966, compound

HRID 2055043Notes

Reaction equation

HRID 2055043 reaction equation
[CH3:1][C:2]1([C:22]2[CH:27]=[CH:26][C:25]([O:28][CH2:29][CH2:30][N:31]3[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]3)=[CH:24][CH:23]=2)[C:19]2[C:18]3[CH:17]=[CH:16][C:15]([OH:20])=[CH:14][C:13]=3[O:12][CH2:11][C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([OH:21])=[CH:5][C:4]=2[O:3]1.[CH3:37][C:38]([CH3:43])([CH3:42])[C:39](Cl)=[O:40].[C:44]([O-:47])(O)=O.[Na+]>ClCCl>[CH3:37][C:38]([CH3:43])([CH3:42])[C:39]([O:20][C:15]1[CH:16]=[CH:17][C:18]2[C:19]3[C:2]([CH3:1])([C:22]4[CH:27]=[CH:26][C:25]([O:28][CH2:29][CH2:30][N:31]5[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]5)=[CH:24][CH:23]=4)[O:3][C:4]4[CH:5]=[C:6]([O:21][C:44](=[O:47])[C:2]([CH3:22])([CH3:19])[CH3:1])[CH:7]=[CH:8][C:9]=4[C:10]=3[CH2:11][O:12][C:13]=2[CH:14]=1)=[O:40]

Participants

5

Reactant 3

HCID 62493Pivaloyl chlorideHCID 516892Sodium BicarbonateHCID 21959282HCID 21959282, compound

Product 1

HCID 21051966HCID 21051966, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 5-methyl-5-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-5,11-dihydro-chromeno[4,3-c]chromene-2,8-diol, prepared as om STEP C above, in dichloromethane (5 mL) (DCM) at 5° C. was added TEA (42 mg, 0.42 mmol) and the reaction mixture stirred for 5 min. Trimethylacetyl chloride (47 mg, 0.39 mmol) was then added to the reaction mixture and the mixture stirred at room temperature overnight. To the reaction mixture was then added saturated NaHCO3 (10 mL) and stirred for 1 h. The resulting mixture was extracted with DCM, washed with brine and dried over MgSO4. The organic layer was concentrated and the residue was purified via silica gel with 2% methanol in DCM as the eluent, to yield the title compound as a thick yellow oil.

Workup

  1. customprepared as om STEP C above
  2. stirringthe mixture stirred at room temperature overnight
  3. extractionThe resulting mixture was extracted with DCM
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. concentrationThe organic layer was concentrated
  7. customthe residue was purified via silica gel with 2% methanol in DCM as the eluent

Sources & evidence

ORD record
ord-d2ef3138159f46ab9fce0e0db73413c2
Source dataset
uspto-grants-2008_02
Patent number
US07329654B2

Reaction notes

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