HCID 10793779, compound → HCID 10817689, compound

HRID 1198762Notes

Reaction equation

HRID 1198762 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)=[C:14]([CH:38]=[O:39])[C:15]([CH2:19][O:20][Si:21]([C:34]([CH3:37])([CH3:36])[CH3:35])([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:46][Mg+].[Br-]>C1COCC1>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([C:40]3[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=3)=[C:14]([CH:38]([OH:39])[CH3:46])[C:15]([CH2:19][O:20][Si:21]([C:34]([CH3:37])([CH3:36])[CH3:35])([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)=[CH:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 10793779HCID 10793779, compoundHCID 178418689HCID 178418689, compound

Product 1

HCID 10817689HCID 10817689, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of aldehyde (1.1 g) from Step 3 in THF (15 mL) at -78° C., was added MeMgBr (1.4M PhMe-THF, 2.8 mL) dropwise. After 10 min, the bath was removed and the reaction mixture quenched with a saturated solution of NH4Cl. The reaction was diluted with Et2O, washed with saturated NH4Cl solution, H2O, brine, dried over MgSO4, and the solvent evaporated to afford the title product as a foam.

Workup

  1. customthe bath was removed
  2. customthe reaction mixture quenched with a saturated solution of NH4Cl
  3. additionThe reaction was diluted with Et2O
  4. washwashed with saturated NH4Cl solution, H2O, brine
  5. dry with materialdried over MgSO4
  6. customthe solvent evaporated

Sources & evidence

ORD record
ord-ac4ebbdfba904a3e96ead8ab87b4af5e
Source dataset
uspto-grants-1994_01
Patent number
US05281720

Reaction notes

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