HCID 10944542, compound → HCID 57126821, compound

HRID 1707875Notes

Reaction equation

HRID 1707875 reaction equation
[CH2:1]([O:8][C@@H:9]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH:10]=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:19]([Mg]Br)[CH2:20][CH:21]=[CH2:22]>CCOCC>[CH2:1]([O:8][C@H:9]([C@@H:10]([OH:11])[CH2:22][CH2:21][CH:20]=[CH2:19])[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 10944542HCID 10944542, compound2×HCID 178418797HCID 178418797, compound

Product 1

HCID 57126821HCID 57126821, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent4×

Procedure

The latter aldehyde was dissolved in Et2O (20 mL). Under anhydrous conditions, the solution of the aldehyde was added dropwise over 15 min to a stirred solution of 3-butenyl magnesium bromide at -78°. The latter solution had been prepared by diluting 71 mL of a 0.64M solution of the Grignard reagent in Et2O with 155 mL of Et2O. After 1 h, the reaction mixture was diluted with Et2O (100 mL). The resulting mixture was washed with a saturated aqueous solution of NH4Cl and then with brine. The organic phase was dried (MgSO4) and evaporated to dryness. The residue was purified by chromatography (SiO2, eluent: hexane-EtOAc, 9:1) to give (2S,3S)-2-benzyloxy-1-phenyl-6-hepten-3-ol (4.82 g), 1H NMR (CDCl3) δ 7.25 (m, 10H), 5.75 (m,1H), 4.95 (m,2H), 4.40 (dd,2H), 3.50 (m, 2H), 2.90 (m,2H), 2.10 (m,3H), 1.60 (m,2H).

Workup

  1. customThe latter solution had been prepared
  2. washThe resulting mixture was washed with a saturated aqueous solution of NH4Cl
  3. dry with materialThe organic phase was dried (MgSO4)
  4. customevaporated to dryness
  5. customThe residue was purified by chromatography (SiO2, eluent: hexane-EtOAc, 9:1)

Sources & evidence

ORD record
ord-1d291acc05914594921e92209f1658d8
Source dataset
uspto-grants-1994_10
Patent number
US05354767

Reaction notes

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