Diethyl [chloro(4-methylphenyl)methyl]phosphonate → (3-Fluoro-5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphth-2-yl)-(4-tolyl)-acetylene

HRID 1382431Notes

Reaction equation

HRID 1382431 reaction equation
Cl[CH:2]([C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=1)P(=O)(OCC)OCC.[F:18][C:19]1[C:20]([CH:33]=O)=[CH:21][C:22]2[C:23]([CH3:32])([CH3:31])[CH2:24][CH2:25][C:26]([CH3:30])([CH3:29])[C:27]=2[CH:28]=1>>[F:18][C:19]1[C:20]([C:33]#[C:2][C:11]2[CH:12]=[CH:13][C:14]([CH3:17])=[CH:15][CH:16]=2)=[CH:21][C:22]2[C:23]([CH3:32])([CH3:31])[CH2:24][CH2:25][C:26]([CH3:29])([CH3:30])[C:27]=2[CH:28]=1

Participants

3

Reactant 2

HCID 13604830Diethyl [chloro(4-methylphenyl)methyl]phosphonateHCID 234989783-Fluoro-2-formyl-5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalene

Product 1

HCID 19786975(3-Fluoro-5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphth-2-yl)-(4-tolyl)-acetylene

Procedure

Using a process similar to that described in Example 13, 27.7 g (0.1 mole) of diethyl 1-chloro-(4-tolyl)-methylphosphonate, 23.4 g (0.1 mole) of 3-fluoro-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 the title compound. Recrystallization from isopropanol gave 16.4 g (51%) of product of melting point 60°-61° C.

Workup

  1. customwere reacted for 1 hour

Sources & evidence

ORD record
ord-f0fbfee7b1a846a489ab4c9698d31e05
Source dataset
uspto-grants-1989_02
Patent number
US04806558

Reaction notes

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