HCID 86624017, compound → HCID 66750500, compound

HRID 643923Notes

Reaction equation

HRID 643923 reaction equation
[Li][CH3:2].[CH3:3][O:4][C:5]1[CH:16]=[CH:15][C:8]([CH2:9][C@@H:10]([CH2:13][CH3:14])[CH:11]=O)=[C:7]([CH:17]=[CH2:18])[CH:6]=1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[CH2:11]([C@@H:10]([CH:13]=[CH2:14])[CH2:9][C:8]1[CH:15]=[CH:16][C:5]([O:4][CH3:3])=[CH:6][C:7]=1[CH:17]=[CH2:18])[CH3:2]

Participants

5

Reactant 2

HCID 86624017HCID 86624017, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 66750500HCID 66750500, compound

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

MeLi (32 mL, 51 mmol, 1.6 M in diethyl ether) is added to a suspension of methyltriphenylphosphonium bromide (27.8 g, 77.8 mmol) in THF (100 mL) at 0° C. The mixture is stirred at 0° C. for 30 min. Then a solution of (R)-2-(4-Methoxy-2-vinylbenzyl)-butyraldehyde (6.12 g) in THF (50 mL) is added. The mixture is stirred at 0° C. for 1 h. The mixture is partitioned between EtOAc and aq. NH4Cl. The organic extract is dried with MgSO4, concentrated and purified to give the title compound as an oil: 1H NMR (CDCl3) δ 0.85 (t, J=7.3 Hz, 3H), 1.23-1.28 (m, 1H), 1.42-1.47 (m, 1H), 2.09-2.14 (m, 1H), 2.56-2.69 (m, 2H), 3.81 (s, 3H), 4.85 (d, J=17 Hz, 1H), 4.93 (dd, J=2, 10 Hz, 1H), 5.27 (dd, J=1, 11 Hz, 1H), 5.50-5.65 (m, 2H), 6.74 (dd, J=3, 8 Hz, 1H), 6.94 (dd, J=11, 17 Hz, 1H), 6.99 (d, J=8 Hz, 1H), 7.02 (d, J=3 Hz, 1H).

Workup

  1. stirringThe mixture is stirred at 0° C. for 1 h
  2. customThe mixture is partitioned between EtOAc and aq. NH4Cl
  3. extractionThe organic extract
  4. dry with materialis dried with MgSO4
  5. concentrationconcentrated
  6. custompurified

Sources & evidence

ORD record
ord-b0f43af49c824047a130690963b141f9
Source dataset
uspto-grants-2010_04
Patent number
US07700633B2

Reaction notes

Loading…