Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Ethyl chloroformate | HCID 10928 | — |
| Reactant | Sodium Azide | HCID 33557 | — |
| Reactant | HCID 13604817 | HCID 13604817 | — |
| Solvent | Acetone | HCID 180 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 131715647 | HCID 131715647 | 79.6% |
Reaction Steps
A solution of 6 ml of triethylamine in 30 ml of acetone is allowed to run into a suspension of 12.7 g (35 mmol) of (E)-4-[2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-7-oxo-naphth-2-yl)-1-propenyl]-benzoic acid (Example 2) in 60 ml of acetone and 20 ml of water, at 0°-5° C. At 0° C. 4.5 ml (5.2 g, 55 mmol) of ethyl chloroformate are added dropwise, the solution is stirred for a further 10 minutes and a solution of 3.5 g (55 mmol) of sodium azide in 7.5 ml of water is then added dropwise. The solution is stirred at 0° C. for a further 2 hours, the finely crystalline solid is filtered off under suction and the residue is washed with a little water and ethanol and dried, to give 10.8 g of the title compound which is processed further without purification (see Example 11).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US04760174 |
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| Source dataset | uspto-grants-1988_07 |
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| ORD ID | ord-ea31aff6d2d84ef2b6f1866160f49747 |
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| Source note | uspto-grants-1988_07 |
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