HCID 57475779, compound → HCID 57475821, compound

HRID 2060778Notes

Reaction equation

HRID 2060778 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]([O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14])[CH2:9][CH:10]=[O:11])[CH:5]=[CH:6][CH:7]=1.[CH2:20]([Mg]Br)[CH:21]=[CH2:22]>C(OCC)C.ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]([O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14])[CH2:9][CH:10]([OH:11])[CH2:22][CH:21]=[CH2:20])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 57475779HCID 57475779, compoundHCID 178455850HCID 178455850, compound

Product 1

HCID 57475821HCID 57475821, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To a 0° C. solution of 3-(3-bromophenyl)-3-(tert-butyldimethylsilyloxy)propanal (17.9 g, 52.1 mmol) in dry diethyl ether (150 mL) is added 1 M allylmagnesium bromide solution in ether (52.1 mL, 52.1 mmol). The resulting mixture is warmed to room temperature over 1 hour. The mixture is diluted with dichloromethane and is quenched by addition of saturated aqueous solution of ammonium chloride. The mixture is extracted three times with dichloromethane. The combined organic layers are washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure to give the title compound as a racemic diastereomeric mixture (18.8 g, 84%). 1H NMR (400 MHz, CDCl3) δ 7.45 (s, 1H), 7.38-7.34 (m, 1H), 7.24-7.21 (m, 1H), 7.19-7.15 (m, 1H), 5.84-5.76 (m, 1H), 5.09-5.04 (m, 1H), 5.00 (t, J=5.3 Hz, 1H), 4.86-4.80 (m, 1H), 3.83-3.75 (m, 2H), 2.23-2.15 (m, 2H), 1.80-1.69 (m, 2H), 0.89 (d, 9H, J=6.6 Hz), 0.06-0.04 (m, 3H), −0.17 (d, J=40.4 Hz, 3H).

Workup

  1. customis quenched by addition of saturated aqueous solution of ammonium chloride
  2. extractionThe mixture is extracted three times with dichloromethane
  3. washThe combined organic layers are washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7eb13c50be3d488f83199c97e906f696
Source dataset
uspto-grants-2012_10
Patent number
US08278441B2

Reaction notes

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