HuagongsheHuagongshe Chemistry Print Report · For research reference only
2,4,6-Trimethylpyridine → (2S,3R)-3-(Triethylsilyloxy)-2-methyl-4-phenylbutanal
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2,4,6-Trimethylpyridine | HCID 7953 | — |
| Reactant | Triethylsilyl trifluoromethanesulphonate | HCID 2733308 | — |
| Reactant | (2R,3R)-2-Methyl-3-phenylmethyloxiranemethanol | HCID 14142342 | — |
| Reactant | (2R,3R)-3-[t-Butyldimethylsilyloxy)-2-methylhexanal | HCID 14959487 | — |
| Product | (2S,3R)-3-(Triethylsilyloxy)-2-methyl-4-phenylbutanal | HCID 14959488 | 80% |
Reaction Steps
Epoxy alcohol 10, 1.2 eq of TESOTf, and 1.5 eq of collidine were reacted as in the preparation of 16 give 80% of aldehyde 11. 1H NMR (CDCl3, 500.35 MHz) δ:9.64 (1H, d J=0.77 Hz), 7.30-7.05 (5H,m) 4.37 (1H, J=3.06, 10.40 Hz), 2.76 (1H, d J=6.64 Hz), 2.75 (2H, d J=7.42 Hz), 2.27 (1H, qdd, J=7.00, 3.38, 0.77 Hz), 1.10 (3H, d, J=7.04 Hz), 0.95-0.75 (6H, m), 0.6-0.4 (9H, m). 1H NMR integration of δ 9.64 to the contaminant δ 9.71 indicated a 93.6:6.4 ratio.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05426206 |
| Source dataset | uspto-grants-1995_06 |
| ORD ID | ord-d773e9f84526488aa202ec27d54f5330 |
| Source note | uspto-grants-1995_06 |