Sodium hydride → 1-Ethoxy-2-fluoro-4-(4-(4-pentylcyclohexyl)cyclohexyl)methyloxybenzene

HRID 1368798Notes

Reaction equation

HRID 1368798 reaction equation
I[CH2:2][CH:3]1[CH2:8][CH2:7][CH:6]([CH:9]2[CH2:14][CH2:13][CH:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:11][CH2:10]2)[CH2:5][CH2:4]1.[CH2:20]([O:22][C:23]1[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][C:24]=1[F:30])[CH3:21].[H-].[Na+]>C1COCC1>[CH2:20]([O:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][CH2:2][CH:3]2[CH2:8][CH2:7][CH:6]([CH:9]3[CH2:14][CH2:13][CH:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:11][CH2:10]3)[CH2:5][CH2:4]2)=[CH:25][C:24]=1[F:30])[CH3:21]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 185172691-Iodomethyl-4-(4-pentylcyclohexyl)cyclohexaneHCID 185172764-Ethoxy-3-fluorophenol

Product 1

HCID 185172881-Ethoxy-2-fluoro-4-(4-(4-pentylcyclohexyl)cyclohexyl)methyloxybenzeneYield 39%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-Iodomethyl-4-(4-pentylcyclohexyl)cyclohexane (9.8 g, 26 mmol) was reacted with 4-ethoxy-3-fluorophenol (3.7 g, 24 mmol) in THF (60 ml) in the presence of NaH (ca. 24 mmol) used as a base. After treatment was carried out by the same method as in Example 3 to obtain 1-ethoxy-2-fluoro-4-(4-(4-pentylcyclohexyl)cyclohexyl)methyloxybenzene (yield: 39%).

Sources & evidence

ORD record
ord-6fbb2d0b401240f58ee5338ba8860f50
Source dataset
uspto-grants-2003_06
Patent number
US06576303B1

Reaction notes

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