trans-3-hydroxy-6-cyano-3,4-dihydro-2,2-dimethyl-4-(1,2-dihydro-2-oxo-4-t-butyldimethylsilyloxymethyl-1-pyridinyl)-2H-benzo[b]pyran → 6-trifluoromethyl-2,2-dimethyl-4-(1,2-dihydro-2-oxo-4-t-butyldimethylsilyloxymethyl-1-pyridinyl)-2H-benzo[b]pyran

HRID 487656Notes

Reaction equation

HRID 487656 reaction equation
O[C@@H]1C(C)(C)OC2C=CC(C#N)=CC=2[C@H]1N1C=CC(CO[Si](C(C)(C)C)(C)C)=CC1=O.O[C@@H:33]1[C:38]([CH3:40])([CH3:39])[O:37][C:36]2[CH:41]=[CH:42][C:43]([C:45]([F:48])([F:47])[F:46])=[CH:44][C:35]=2[C@H:34]1[N:49]1[CH:54]=[CH:53][C:52]([CH2:55][O:56][Si:57]([C:60]([CH3:63])([CH3:62])[CH3:61])([CH3:59])[CH3:58])=[CH:51][C:50]1=[O:64]>>[F:48][C:45]([F:46])([F:47])[C:43]1[CH:42]=[CH:41][C:36]2[O:37][C:38]([CH3:39])([CH3:40])[CH:33]=[C:34]([N:49]3[CH:54]=[CH:53][C:52]([CH2:55][O:56][Si:57]([C:60]([CH3:62])([CH3:63])[CH3:61])([CH3:59])[CH3:58])=[CH:51][C:50]3=[O:64])[C:35]=2[CH:44]=1

Participants

3

Reactant 2

HCID 131718356trans-3-hydroxy-6-cyano-3,4-dihydro-2,2-dimethyl-4-(1,2-dihydro-2-oxo-4-t-butyldimethylsilyloxymethyl-1-pyridinyl)-2H-benzo[b]pyranHCID 131718360trans-3-hydroxy-6-trifluoromethyl-3,4-dihydro-2,2-dimethyl-4-(1,2-dihydro-2-oxo-4-t-butyldimethylsilyloxymethyl-1-pyridinyl)-2H-benzo[b]pyran

Product 1

HCID 217469266-trifluoromethyl-2,2-dimethyl-4-(1,2-dihydro-2-oxo-4-t-butyldimethylsilyloxymethyl-1-pyridinyl)-2H-benzo[b]pyran

Procedure

The reaction and after treatment of Example 8 are repeated, except that the trans-3-hydroxy-6-cyano-3,4-dihydro-2,2-dimethyl-4-(1,2-dihydro-2-oxo-4-t-butyldimethylsilyloxymethyl-1-pyridinyl)-2H-benzo[b]pyran used in Example 8 is replaced with the trans-3-hydroxy-6-trifluoromethyl-3,4-dihydro-2,2-dimethyl-4-(1,2-dihydro-2-oxo-4-t-butyldimethylsilyloxymethyl-1-pyridinyl)-2H-benzo[b]pyran obtained in Example 50. Thus, 6-trifluoromethyl-2,2-dimethyl-4-(1,2-dihydro-2-oxo-4-t-butyldimethylsilyloxymethyl-1-pyridinyl)-2H-benzo[b]pyran is obtained.

Workup

  1. customThe reaction

Sources & evidence

ORD record
ord-a050b0d9c48946d8b8c1802e94f306bb
Source dataset
uspto-grants-1994_03
Patent number
US05296492

Reaction notes

Loading…