Methyltriphenylphosphonium iodide → HCID 69957465, compound

HRID 1937136Notes

Reaction equation

HRID 1937136 reaction equation
[I-].[CH3:2][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].C1(C)C=CC=CC=1.[CH3:39][O:40][C@H:41]1[C@@H:45]2[CH2:46][C@H:47]3[C@H:52]([C:53](=O)[C@@H:44]2[C@@H:43]([CH3:55])[O:42]1)[CH2:51][CH2:50][CH2:49][CH2:48]3>>[CH3:39][O:40][C@H:41]1[C@@H:45]2[CH2:46][C@H:47]3[C@H:52]([C:53](=[CH2:2])[C@@H:44]2[C@@H:43]([CH3:55])[O:42]1)[CH2:51][CH2:50][CH2:49][CH2:48]3

Participants

4

Reactant 3

HCID 638159Methyltriphenylphosphonium iodideHCID 23702675Sodium bis(trimethylsilyl)amide tolueneHCID 69957533HCID 69957533, compound

Product 1

HCID 69957465HCID 69957465, compoundYield 88%

Procedure

Similarly to Example 7, 6665.6 mg(5 equivalents) of methyltriphenylphosphonium iodide and 16.5 ml(5 equivalents) of sodium bis(trimethylsilyl)amide-toluene solution(1M) were reacted with 786.0 mg of (1R,3R,3aS,4aR,8aS,9aR)-1-methoxy-3-methyl-4-oxo-dodecahydronaphtho[2,3-c]furan to obtain 683.5 mg of (1R,3R,3aR,4aR,8aS,9aR)-1-methoxy-3-methyl-4-methylene-dodecahydronaphtho[2,3-c]furan(yield 88%).

Sources & evidence

ORD record
ord-c96bb7714d0e41af826dd1a01755d5c5
Source dataset
uspto-grants-2002_05
Patent number
US06392059B1

Reaction notes

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