Boron trifluoride etherate → HCID 91042603, compound

HRID 1372182Notes

Reaction equation

HRID 1372182 reaction equation
[SiH](CC)(CC)CC.B(F)(F)F.[CH3:12][CH2:13][O:14]CC.[O:17]([C@H:25]1[CH2:32][C@H:28]2[O:29][CH2:30][CH2:31][C@@H:27]2[CH2:26]1)[Si](C(C)(C)C)(C)C>C(Cl)Cl>[O:29]1[CH2:30][CH2:31][C@H:27]2[CH2:26][C@H:25]([O:17][C:13](=[O:14])[CH3:12])[CH2:32][C@H:28]12

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 12052TriethylsilaneHCID 67053293HCID 67053293, compound

Product 1

HCID 91042603HCID 91042603, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the bicyclic ether (228 mg, 1.065 mmol) and Et3SiH (370 mg, 3.196 mmol) in CH2Cl2 (5 mL) at room temperature, was added BF3.OEt2 (450 mg, 3.196 mmol) following the same reaction conditions as described in the synthesis of compound 3 to obtain compound 5 (140 mg, 58% three steps) as an oil. 1H NMR (CDCl3, 200 MHz): δ 5 (m, 1H), 4.5 (m, 1H), 3.95 (m, 1H), 3.74 (m, 1H), 2.7 (m, 1H), 2.1 (m, 3H), 2 (s, 3H), 1.5–1.9 (m, 3H).

Workup

  1. customthe same reaction conditions

Sources & evidence

ORD record
ord-8113e1edf305448ab6cc3cd7747224dd
Source dataset
uspto-grants-2007_01
Patent number
US07157489B2

Reaction notes

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