Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Lithium borohydride | HCID 4148881 | — |
| Reactant | HCID 19389895 | HCID 19389895 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 67793839 | HCID 67793839 | 65.5% |
Reaction Steps
Lithium borohydride (11 mg) was added to a solution of 2-ethoxycarbonyl-4-([2'-(2-triphenylmethyl-2H-tetrazol-5-yl)biphenyl-4-yl]methoxy)quinoline (346 mg) in tetrahydrofuran (4 ml) and the mixture stirred for 18 hours. Water (20 ml) was added to the mixture and a white solid precipitated. The solid was collected by filtration, dissolved in ethyl acetate and the solution dried (MgSO4). The solvent was removed by evaporation and the residue crystallised from ethyl acetate/hexane to give 2-hydroxymethy-4-([2'-(2-triphenylmethyl-2H-tetrazol-5-yl)biphenyl-4-yl]methoxy)quinoline (213 mg), as a white crystalline solid, m.p. 183°-185° C. (dec.); NMR: 4.85(s,2H), 5.18(s,2H), 6.70(s,1H), 6.85-6.98(m,6H), 7.15-7.35(m,13H), 7.35-7.58(m,4H), 7.70(dt,1H), 7.95-8.08(m,2H), 8.15(d,1H); microanalysis, found: C,78.7; H,4.7; N,10.7%; C43H 33 N5O2 requires C,79.2; H,5.1; N,10.7%.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05444071 |
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| Source dataset | uspto-grants-1995_08 |
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| ORD ID | ord-e5a6e8f474174c3092cbef08ac3d3e52 |
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| Source note | uspto-grants-1995_08 |
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