2-Naphthalenecarboxaldehyde, 3-ethyl-5,6,7,8-tetrahydro-5,5,8,8-tetramethyl- → (3-Ethyl-5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphth-2-yl)-(4-tolyl)-acetylene

HRID 982052Notes

Reaction equation

HRID 982052 reaction equation
Cl[CH:2](P(=O)(OCC)OCC)[C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][CH:4]=1.[CH2:18]([C:20]1[C:21]([CH:34]=O)=[CH:22][C:23]2[C:24]([CH3:33])([CH3:32])[CH2:25][CH2:26][C:27]([CH3:31])([CH3:30])[C:28]=2[CH:29]=1)[CH3:19]>>[CH2:18]([C:20]1[C:21]([C:34]#[C:2][C:3]2[CH:4]=[CH:5][C:6]([CH3:9])=[CH:7][CH:8]=2)=[CH:22][C:23]2[C:24]([CH3:33])([CH3:32])[CH2:25][CH2:26][C:27]([CH3:31])([CH3:30])[C:28]=2[CH:29]=1)[CH3:19]

Participants

3

Reactant 2

HCID 426742-Naphthalenecarboxaldehyde, 3-ethyl-5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-HCID 13604830Diethyl [chloro(4-methylphenyl)methyl]phosphonate

Product 1

HCID 19786969(3-Ethyl-5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphth-2-yl)-(4-tolyl)-acetyleneYield 25.1%

Procedure

Using a process similar to that described in Example 13, 27.7 g (0.1 mole) of diethyl 1-chloro-1-(4-tolyl)-methylphosphonate, 24.4 g (0.1 mole) of 3-ethyl-2-formyl-5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalene and 22.5 g (0.2 mole) of potassium tert.-butylate were reacted for 1 hour to give 8.3 g (25%) of the title compound of melting point 72°-73° C., the reaction mixture being poured onto water and acidified, and the precipitate which had separated out being recrystallized from methanol and once again from isopropanol.

Workup

  1. customwere reacted for 1 hour

Sources & evidence

ORD record
ord-61796fc6a32144df9417c1fcc45feef6
Source dataset
uspto-grants-1991_02
Patent number
US04994489

Reaction notes

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