HCID 11189560, compound → HCID 69031670, compound

HRID 750472Notes

Reaction equation

HRID 750472 reaction equation
[CH3:1][C:2]1([CH3:32])[O:6][C@H:5]([C:7](=[O:29])[CH2:8][O:9][C:10]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C@H:4]([CH:30]=[CH2:31])[O:3]1.[CH:33]([Mg]Br)=[CH2:34]>O1CCCC1>[CH3:1][C:2]1([CH3:32])[O:6][C@H:5]([C@@:7]([OH:29])([CH:33]=[CH2:34])[CH2:8][O:9][C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C@H:4]([CH:30]=[CH2:31])[O:3]1

Participants

4

Reactant 2

HCID 11189560HCID 11189560, compoundHCID 178418507HCID 178418507, compound

Product 1

HCID 69031670HCID 69031670, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 4 (14.66 g, 34.22 mmol) in tetrahydrofuran (150 ml) was added dropwise vinylmagnesium bromide (68.44 ml, 68.44 mmol, 1.0 M solution in tetrahydrofuran) at −78° C., and the reaction mixture was stirred for 1 hour at the same temperature. The reaction mixture was quenched by saturated ammonium chloride solution and brine, and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, filtered, and evaporated. The resulting oil was purified by column chromatography (hexane:ethyl acetate=9:1) to give 5 (15.62 g, 100%) as a white semi-solid; 1H NMR (400 MHz, CDCl3) δ 7.43-7.22 (m, 15H), 6.16 (dd, J=17.2, 10.8 Hz, 1H), 6.01-5.93 (m, 1H), 5.42 (dd, J=17.2, 1.2 Hz, 1H), 5.27 (dd, J=10.8, 1.2 Hz, 1H), 4.99 (d, J=16.0 Hz, 1H), 4.98 (d, J=11.2 Hz, 1H), 4.54-4.47 (m, 2H), 3.33 (d, J=8.8 Hz, 1H), 3.05 (d, J=8.4 Hz, 1H), 2.54 (bs, 1H), 1.46 (s, 3H), 1.40 (s, 3H).

Workup

  1. customThe reaction mixture was quenched by saturated ammonium chloride solution and brine
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe resulting oil was purified by column chromatography (hexane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-43781932c4c1497d9ab502eb9289b4c3
Source dataset
uspto-grants-2008_07
Patent number
US07405214B2

Reaction notes

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