2,4,6-Trimethylpyridine → (2S,3R)-3-(Triethylsilyloxy)-2-methyl-4-phenylbutanal

HRID 22076

反応式

HRID 22076 の反応式
[CH3:1][C@@:2]1([CH2:12][OH:13])[C@@H:4]([CH2:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[O:3]1.[Si:14](OS(C(F)(F)F)(=O)=O)([CH2:19][CH3:20])([CH2:17][CH3:18])[CH2:15][CH3:16].N1C(C)=CC(C)=CC=1C.[Si](O[C@H](CCC)[C@@H](C)C=O)(C(C)(C)C)(C)C>>[CH2:15]([Si:14]([CH2:19][CH3:20])([CH2:17][CH3:18])[O:3][C@H:4]([CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C@H:2]([CH3:1])[CH:12]=[O:13])[CH3:16]

参加物

5

反応物 4

HCID 79532,4,6-TrimethylpyridineHCID 2733308Triethylsilyl trifluoromethanesulphonateHCID 14142342(2R,3R)-2-Methyl-3-phenylmethyloxiranemethanolHCID 14959487(2R,3R)-3-[t-Butyldimethylsilyloxy)-2-methylhexanal

生成物 1

HCID 14959488(2S,3R)-3-(Triethylsilyloxy)-2-methyl-4-phenylbutanal収率 80%

実験手順

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.

出典と根拠

ORDレコード
ord-d773e9f84526488aa202ec27d54f5330
出典データセット
uspto-grants-1995_06
特許番号
US05426206

関連ノート

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