Tetrahydrofuran → 4-[3-Hydroxy-3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-1-propynyl]benzenemethanol
Reaction equation
C([O:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]#[C:13][CH:14]([OH:29])[C:15]2[CH:24]=[CH:23][C:22]3[C:21]([CH3:26])([CH3:25])[CH2:20][CH2:19][C:18]([CH3:28])([CH3:27])[C:17]=3[CH:16]=2)=[CH:8][CH:7]=1)(=O)C.C1COCC1.[OH-].[Na+]>O>[OH:29][CH:14]([C:15]1[CH:24]=[CH:23][C:22]2[C:21]([CH3:26])([CH3:25])[CH2:20][CH2:19][C:18]([CH3:28])([CH3:27])[C:17]=2[CH:16]=1)[C:13]#[C:12][C:9]1[CH:8]=[CH:7][C:6]([CH2:5][OH:4])=[CH:11][CH:10]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
780 mg (2 mmol) of 4-[3-hydroxy-3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-1-propynyl]benzyl acetate and 30 ml of THF were introduced into a round-bottomed flask. 5 ml of a 2N methanolic sodium hydroxide solution were added and stirring was carried out for 30 min. The reaction mixture was poured into water and extracted with ethyl ether. The organic phase was separated by settling, dried over magnesium sulfate and evaporated. The residue obtained was triturated in heptane and filtered, 419 mg (60%) of the expected compound, with a melting point of 85°-86° C., were recovered.
Workup
- extractionextracted with ethyl ether
- customThe organic phase was separated
- dry with materialdried over magnesium sulfate
- customevaporated
- customThe residue obtained
- customwas triturated in heptane
- filtrationfiltered
- custom419 mg (60%) of the expected compound, with a melting point of 85°-86° C., were recovered
Sources & evidence
- ORD record
- ord-306faf762f3f43bfbe053710b60e0e30
- Source dataset
- uspto-grants-2002_04
- Patent number
- US06368608B1
Reaction notes
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