3-(2-Chlorophenyl)propanal → HCID 86644265, compound

HRID 1886861Notes

Reaction equation

HRID 1886861 reaction equation
Cl[C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[CH2:4][CH2:5][CH:6]=[O:7].[CH:12]1(/[CH:18]=[CH:19]/[C:20](=[O:26])[C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1>C(Cl)(Cl)Cl>[CH2:4]([C@@H:5]1[C:6](=[O:7])[O:26][C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:19][C@@H:18]1[CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)[C:3]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:2]=1

Participants

4

Reactant 2

HCID 218597263-(2-Chlorophenyl)propanalHCID 86644266HCID 86644266, compound

Product 1

HCID 86644265HCID 86644265, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Prepared according to the general procedure from 2-chloro-hydrocinnamaldehyde and (E)-ethyl 4-cyclohexyl-2-oxobut-3-enoate using 2 mol % 1 as the catalyst in 85% yield as a single diastereomer (colorless oil). [α]D20 (c 1.20, CHCl3)=+83.5; 1H NMR (400 MHz, CDCl3) δ 7.33-7.21 (m, 5H), 6.48 (d, 1H, J=6.5 Hz), 4.30 (dq, 1H, J=7.2, 1.8 Hz), 3.38 (dd, 1H, J=14.3, 5.7 Hz), 2.97-2.91 (m, 1H), 2.77 (dd, 1H, J=14.3, 9.1 Hz), 2.45-2.41 (m, 1H), 1.76-1.62 (m, 5H), 1.47-1.44 (m, 1H), 1.34 (t, 3H, J=7.2 Hz), 1.27-1.06 (m, 4H), 0.93-0.89 (m, 1H); 13C NMR (100 MHz, CDCl3) δ 170.4, 160.7, 142.8, 138.6, 128.9, 126.9, 117.6, 62.0, 43.0, 39.4, 37.7, 31.7, 31.4, 27.2, 26.8, 26.1, 14.3; IR (thin film) ν 3520, 3086, 3028, 2981, 2928, 2853, 1770, 1731, 1660, 1453, 1369, 1309, 1262, 1120, 1094, 1013 cm−1; HRMS (ESI) calcd for C21H26O4 [M+Na]+ 365.1723, found 365.1721; 95% ee (4S,5S)-isomer as determined by HPLC (AS-H, 20:1 hexanes/i-PrOH), tr (4S,5S)=19.1 min, tr (4R,5R)=15.7 min.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-5e83ccb9123e45aab74321f142c4d0da
Source dataset
uspto-grants-2013_08
Patent number
US08501658B2

Reaction notes

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