HCID 12279310, compound → HCID 86644263, compound

HRID 1886855Notes

Reaction equation

HRID 1886855 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].[O:12]=[C:13]([CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1)/[CH:14]=[CH:15]/[C:16]([O:18][CH3:19])=[O:17]>C(Cl)(Cl)Cl>[CH2:4]([C@H:5]1[C@@H:15]([C:16]([O:18][CH3:19])=[O:17])[CH:14]=[C:13]([CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)[O:12][C:6]1=[O:7])[C:3]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:2]=1

Participants

4

Reactant 2

HCID 12279310HCID 12279310, compoundHCID 218597263-(2-Chlorophenyl)propanal

Product 1

HCID 86644263HCID 86644263, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Prepared according to the general procedure from 2-chloro-hydrocinnamaldehyde and (E)-methyl 4-oxo-4-cyclohexylbut-2-enoate using 0.5 mol % 1 as the catalyst in 76% yield as a single diasteromer (white solid). [α]D20 (c 1.06, CHCl3)=+178.6; mp=87-89° C.; 1H NMR (400 MHz, CDCl3) δ 7.32-7.25 (m, 3H), 7.15-7.13 (m, 2H), 4.98 (d, 1H, J=6.9 Hz), 3.73 (s, 3H), 3.47 (dd, 1H, J=14.3, 4.8 Hz), 3.06 (t. 1H, J=6.3 hz), 2.86-2.81 (m, 1H), 2.67 (dd, 1H, J=14.3, 10.1 Hz), 2.06-2.03 (m, 1H), 1.88-1.83 (m, 5H), 1.28-1.13 (m, 5H); 13C NMR (100 MHz, CDCl3) δ 171.4, 169.6, 170.3, 138.3, 129.1, 128.9, 127.0, 96.2, 52.6, 43.0, 41.0, 40.0, 33.4, 30.2, 30.0, 26.1, 26.0, 25.9; IR (thin film) ν 3086, 3027, 2929, 2854, 1773, 1737, 1452, 1436, 1155, 1056 cm−1; HRMS (ESI) calcd for C20H24O4 [M+Na]+ 351.1566, found 351.1574; 86% ee (3S,4S)-isomer as determined by HPLC(OD-H, 9:1 hexanes/i-PrOH), tr (3S,4S)=8.5 min, tr (3R,4R)=7.7 min.

Workup

  1. customPrepared
  2. customtr (3S,4S)=8.5 min, tr (3R,4R)=7.7 min.

Sources & evidence

ORD record
ord-06407b683aa74c5ebdee0ce266f80ea5
Source dataset
uspto-grants-2013_08
Patent number
US08501658B2

Reaction notes

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