Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Iodide | HCID 5238 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 2-Butyn-1-ol, 4-chloro- | HCID 202775 | — |
| Reactant | 7-Octynoic acid methyl ester | HCID 554083 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 86704358 | HCID 86704358 | 63.3% |
Reaction Steps
23.00 g (0.22 mol) of 4-chloro-2-butyn-1-ol (I), 33.93 g (0.22 mol) of methyl 7-octynoate (II), 30.41 g (0.22 mol) of K2CO3, 32.98 g (0.22 mol) of NaI, and 20.95 g (0.11 mol) of CuI were added to 440 ml of DMF, followed by stirring at 30° C. for 48 hours. The reaction mixture was quenched by adding to a saturated aqueous NH4Cl solution (200 ml) (hereinafter, referred to as “sat. NH4Cl aq.”), then the resulting mixture was extracted with ethyl acetate. The extract was washed with water, concentrated, and the concentrate was purified over a silica gel column (hexane/ethyl acetate=8/2 to 4/6 (volume ratio)) to obtain 30.97 g of methyl 12-hydroxydodeca-7,10-diynoate having a GC purity of 93.3% (yield: 59.1% th). The structure thereof was confirmed by NMR.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09085545B2 |
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| Source dataset | uspto-grants-2015_07 |
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| ORD ID | ord-dbf192bd41434d85a45395fab143e430 |
|---|
| Source note | uspto-grants-2015_07 |
|---|
