Dichloromethane → HCID 14769336, compound

HRID 617119Notes

Reaction equation

HRID 617119 reaction equation
[CH2:1]([O:8][CH2:9][C:10]1C=CC=[CH:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Mg]I.C(Cl)Cl.C1C[O:25]CC1>[Cu]I>[CH2:1]([O:8][CH2:9][C@@H:10]([OH:25])[CH2:11][CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 7657Dibenzyl etherHCID 8028Tetrahydrofuran2×HCID 178418373HCID 178418373, compound

Product 1

HCID 14769336HCID 14769336, compound

Reagents, catalysts & solvents 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst

Conditions

Temperature
-78 °C

Procedure

To a mixture of the benzyl ether above (44 g, 0.268 mol) and CuI (51 g, 0.268 mol) in anhydrous THF (1 L) was slowly added MeMgI (270 mL of a 3 M THF solution, 0.810 mol) at -78° C. The mixture was stirred at -78° C. for 4 hours and was warmed to room temperature. After aqueous work-up (CH2Cl2) and chromatography, 47.0 g of the title compound was obtained: [α]25D +8.2° (c 1.2, CHCl3). IR: 3428. 1H NMR (CDCl3): δ0.94 (3H, t, J=7.5), 1.47 (2H, m), 2.38 (1H, br), 3.32 (1H, dd, J=8.0, 9.3), 3.50 (1H, dd, J=2.9, 9.3), 3.73 (1H, m), 4.54 (2H, s), 7.26-7.36 (5H, m). 13C NMR (CDCl3): δ9.8, 26.1, 71.7, 73.3, 74.3, 127.7, 127.7, 128.4, 138.0. HRMS (EI) calcd for C11H16O2 180.1150, found 180.1145.

Workup

  1. customat -78° C
  2. temperaturewas warmed to room temperature

Sources & evidence

ORD record
ord-6ff5a446ab0f41fdbb1d34dbb84abc4d
Source dataset
uspto-grants-1999_09
Patent number
US05948770

Reaction notes

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