Ethyl 4-iodobenzoate → Ethyl 4-[3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-1-propynyl]benzoate

HRID 428223Notes

Reaction equation

HRID 428223 reaction equation
[CH3:1][C:2]1([CH3:17])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([CH2:14][C:15]#[CH:16])[CH:5]=[CH:4][C:3]1=2.I[C:19]1[CH:29]=[CH:28][C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:21][CH:20]=1>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu](I)I.C(N(CC)CC)C>[CH3:1][C:2]1([CH3:17])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]2[CH:7]=[C:6]([CH2:14][C:15]#[C:16][C:19]3[CH:29]=[CH:28][C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:21][CH:20]=3)[CH:5]=[CH:4][C:3]1=2

Participants

6

Reactant 2

HCID 142891Ethyl 4-iodobenzoateHCID 177738693-(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-1-propyne

Product 1

HCID 18357924Ethyl 4-[3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-1-propynyl]benzoate

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Procedure

7.4 g (32.7 mmol) of 3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-1-propyne, 8.2 g (29.7 mmol) of ethyl 4-iodobenzoate and 50 ml of triethylamine are introduced into a three-necked flask under a stream of nitrogen. The reaction medium is degassed by bubbling nitrogen through, 360 mg (0.5 mmol) of bis(triphenylphosphine)palladium(II) chloride and 130 mg of copper iodide are introduced and the mixture is stirred at room temperature for eight hours. The reaction medium is evaporated to dryness, the residue is taken up in ethyl acetate and hydrochloric acid (1 N) and the organic phase is separated out after settling has taken place, dried over magnesium sulphate and evaporated. The residue is purified by chromatography on a column of silica eluted with a mixture of heptane and ethyl acetate (70/30). After evaporation of the solvents, a solid is collected which is triturated from heptane, filtered and dried. 9.3 g (84%) of the expected ethyl ester are collected, with a melting point of 59-60° C.

Workup

  1. customThe reaction medium is degassed
  2. additionare introduced
  3. customThe reaction medium is evaporated to dryness
  4. customhydrochloric acid (1 N) and the organic phase is separated out after settling
  5. dry with materialdried over magnesium sulphate
  6. customevaporated
  7. customThe residue is purified by chromatography on a column of silica
  8. washeluted with a mixture of heptane and ethyl acetate (70/30)
  9. customAfter evaporation of the solvents
  10. customa solid is collected which
  11. customis triturated from heptane
  12. filtrationfiltered
  13. customdried
  14. custom9.3 g (84%) of the expected ethyl ester are collected, with a melting point of 59-60° C.

Sources & evidence

ORD record
ord-761cf75396e14564bf539588b07034b3
Source dataset
uspto-grants-2001_11
Patent number
US06313162B1

Reaction notes

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