HCID 59445892, compound → HCID 86644268, compound

HRID 1886863Notes

Reaction equation

HRID 1886863 reaction equation
[Si:1]([O:8][CH2:9][CH:10](Cl)[CH:11]=[O:12])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[O:14]=[C:15](/[CH:21]=[CH:22]/[C:23]1[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=1)[C:16]([O:18][CH2:19][CH3:20])=[O:17]>C(Cl)(Cl)Cl>[Si:1]([O:8][CH2:9][C@@H:10]1[C:11](=[O:12])[O:14][C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:21][C@@H:22]1[C:23]1[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 59445892HCID 59445892, compoundHCID 714256453-{[tert-Butyl(dimethyl)silyl]oxy}-2-chloropropanal

Product 1

HCID 86644268HCID 86644268, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Prepared according to the general procedure from 3-(tert-butyldimethylsilyloxy)-2-chloropropanal and (E)-ethyl 2-oxo-4-p-tolylbut-3-enoate using 2 mol % 1 as the catalyst in 83% yield as a single diastereomer (white solid). [α]D2 (c 1.27, CHCl3)=+244.6; mp=60-61° C.; 1H NMR (400 MHz, CDCl3) δ 7.32-7.24 (m, 3H), 7.12 (d, 2H, J=8.1 Hz), 6.99 (d, 2H, J=8.1 hz), 6.70 (d, 1H, J=7.5 Hz), 4.32 (q, 1H, J=7.2 Hz), 3.77 (t, 1H, J=6.8 Hz), 2.81 (q, 1H, J=6.8 Hz), 2.33 (s, 3H), 1.72-1.63 (m, 2H), 1.37-1.14 (m, 19H), 0.88 (t, 3H, J=6.8 Hz); 13C NMR (100 MHz, CDCl3) δ 167.3, 160.7, 142.6, 138.2, 132.0, 129.8, 128.5, 118.9, 62.1, 58.7, 45.8, 38.3, 26.0, 21.3, 18.3, 14.4, −5.3, −5.4; IR (thin film) ν 3027, 2953, 2929, 2857, 1776, 1740, 1658, 1471, 1370, 1317, 1262, 1084 cm−1; HRMS (EI) calcd for C25H36O4 [M-Bu]+ 347.1315, found 347.1305; 95% ee (4S,5R)-isomer as determined by HPLC (AD-H, 100:1 hexanes/i-PrOH), tr (4S,5R)=8.5 min, tr (4R,5S)=10.0 min.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-92b9357b40ce4ebb868ad7d28c6f17a8
Source dataset
uspto-grants-2013_08
Patent number
US08501658B2

Reaction notes

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