Tetrahydrofuran → HCID 10666472, compound

HRID 1198758Notes

Reaction equation

HRID 1198758 reaction equation
[CH3:1][O:2][CH:3]([O:19][CH3:20])[C:4]1[CH:9]=[C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:7]=[CH:6][C:5]=1Br.[Li][CH2:22][CH2:23][CH2:24]C.[CH2:26]1[CH2:30][O:29][CH2:28][CH2:27]1>CCCCCC>[CH3:1][O:2][CH:3]([O:19][CH3:20])[C:4]1[CH:9]=[C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:7]=[CH:6][C:5]=1[CH:28]([OH:29])[C:27]1[CH:26]=[CH:30][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 18398840HCID 18398840, compoundHCID 178418339Butyllithium

Product 1

HCID 10666472HCID 10666472, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
-10 °C

Procedure

To a solution of 2-bromo-5-benzyloxy benzaldehyde dimethylacetal (Tet. Lett., 22, 5027 (1981)) (130 g) in THF (2.0 L), cooled to -78° C., was added dropwise a solution of n-BuLi (210 ml, 1.91 M) in hexane. After 15 min., a solution of benzalde48 mL) in THF (50 ml) was added dropwise. The cooling bath was removed, then the reaction mixture was warmed slowly (40 min.) to -10° C. and quenched with a saturated NH4Cl solution. The reaction mixture was diluted with Et2O (2.0 L). The organic phase decanted, washed with H2O (3×), brine, dried over MgSO4 and the solvents evaporated. The residue was chromatographed on silica gel (hexane/EtOAc 95:5 to 85:15) to give the title product as a foam.

Workup

  1. customThe cooling bath was removed
  2. customquenched with a saturated NH4Cl solution
  3. additionThe reaction mixture was diluted with Et2O (2.0 L)
  4. customThe organic phase decanted
  5. washwashed with H2O (3×), brine
  6. dry with materialdried over MgSO4
  7. customthe solvents evaporated
  8. customThe residue was chromatographed on silica gel (hexane/EtOAc 95:5 to 85:15)

Sources & evidence

ORD record
ord-99b2c742c1ac4ae4a0679bb3f8f56224
Source dataset
uspto-grants-1994_01
Patent number
US05281720

Reaction notes

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