Sodium hydride → HCID 86761050, compound

HRID 1994226Notes

Reaction equation

HRID 1994226 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:5]=[C:6]([CH:21]=[C:22]([F:24])[CH:23]=1)[C:7]([C:13]1[CH:18]=[C:17]([F:19])[CH:16]=[C:15]([F:20])[CH:14]=1)([OH:12])[C:8]([O:10][CH3:11])=[O:9].[C@@:25]12(O)[N:32](C)[C@@H:29]([CH2:30][CH2:31]1)[CH2:28][CH:27]=[CH:26]2>C1(C)C=CC=CC=1>[F:3][C:4]1[CH:5]=[C:6]([CH:21]=[C:22]([F:24])[CH:23]=1)[C:7]([C:13]1[CH:18]=[C:17]([F:19])[CH:16]=[C:15]([F:20])[CH:14]=1)([OH:12])[C:8]([O:10][C@@:11]12[N:32]([CH3:25])[C@@H:29]([CH2:30][CH2:31]1)[CH2:28][CH:27]=[CH:26]2)=[O:9]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 22574235HCID 22574235, compoundHCID 53629842Tropenol

Product 1

HCID 86761050HCID 86761050, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

1.53 g (0.0636 mol) of NaH are placed in 30 ml of toluene, a solution of 14 g (0.0446 mol) of 3j and 8.85 g (0.0636 mol) of tropenol in 80 ml of toluene is added dropwise at 10° C. and 860 mbar. The alcohol produced during the reaction is distilled off while at the same time toluene is added dropwise. After 3 hours, the mixture is cooled and extracted, with dichloromethane and water. The combined organic phases were dried over MgSO4 and evaporated to dryness. The residue was stirred with petroleum ether/ethyl acetate 95:5. Yield: 11.21 g of light beige crystals (60% of theory); melting point: 168° C.-170° C.

Sources & evidence

ORD record
ord-38b97575ff73484d9bfeffb5961e45b8
Source dataset
uspto-grants-2010_01
Patent number
US07652138B2

Reaction notes

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