Methallyltrimethylsilane → HCID 68794579, compound

HRID 1713591Notes

Reaction equation

HRID 1713591 reaction equation
[CH2:1]([Si](C)(C)C)[C:2](=[CH2:4])[CH3:3].[CH2:9]([O:16][C@@H:17]1[C@@H:22]([O:23][CH2:24]C2C=CC=CC=2)[C@H:21]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C@@H:20]([CH2:39][O:40][CH2:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[O:19][C@:18]1([C:49]1[CH:54]=[C:53]([CH2:55][C:56]2[CH:61]=[CH:60][C:59]([CH2:62][CH3:63])=[CH:58][CH:57]=2)[C:52]([Cl:64])=[CH:51][C:50]=1[O:65][CH3:66])O)C1C=CC=CC=1>C(Cl)Cl>[CH2:9]([O:16][C@@H:17]1[C@@H:22]([O:23][CH2:24][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[C@H:21]([O:31][CH2:32][C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[C@@H:20]([CH2:39][O:40][CH2:41][C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=2)[O:19][C@:18]1([C:49]1[CH:54]=[C:53]([CH2:55][C:56]2[CH:61]=[CH:60][C:59]([CH2:62][CH3:63])=[CH:58][CH:57]=2)[C:52]([Cl:64])=[CH:51][C:50]=1[O:65][CH3:66])[CH2:1][C:2]([CH3:3])=[CH2:4])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

4

Reactant 2

HCID 642554MethallyltrimethylsilaneHCID 68794922HCID 68794922, compound

Product 1

HCID 68794579HCID 68794579, compoundYield 104.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of methallyltrimethylsilane (185 μL, 1.05 mmol) and 23 (0.28 g, 0.35 mmol) in anhydrous methylene chloride (10 mL) at −20° C. was added BF3 OEt2 (88 μL, 0.70 mmol) in a drop-wise manner. The resulting light orange mixture was stirred for 1 hour, during which the temperature was allowed to rise to 0° C. The reaction mixture was quenched with 10% NaHCO3 and extracted with DCM. The organic layer was separated, dried (Na2SO4), filtered, and evaporated to yield a residue which was purified by column chromatography eluting with 0-15% EtOAc in petroleum ether to give 24 (153 mg, 52%). 1H NMR (300 MHz, CDCl3) δ 7.18-7.30 (m, 20H), 7.00-7.05 (m, 1H), 6.98 (s, 4H), 6.69 (s, 1H), 4.67 (t, J=10.8 Hz, 1H), 4.49-4.60 (m, 8H), 4.24 (d, J=11.4 Hz, 1H), 4.12 (d, J=6.0 Hz, 1H), 3.67-4.00 (m, 7H), 3.54 (s, 3H), 3.07 (d, J=16.2 Hz, 1H), 2.79 (d, J=15.9 Hz, 1H), 2.55 (q, J=7.5 Hz, 2H), 1.54 (s, 3H), 1.17 (t, J=7.5 Hz, 3H). LC/MS m/z 860 (M+Na).

Workup

  1. customto rise to 0° C
  2. customThe reaction mixture was quenched with 10% NaHCO3
  3. extractionextracted with DCM
  4. customThe organic layer was separated
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated
  8. customto yield a residue which
  9. customwas purified by column chromatography
  10. washeluting with 0-15% EtOAc in petroleum ether

Sources & evidence

ORD record
ord-6d72347d4e6c42628362e8ee31c26de6
Source dataset
uspto-grants-2010_09
Patent number
US07795228B2

Reaction notes

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