2-chlorododecanal → HCID 86644267, compound

HRID 1886862Notes

Reaction equation

HRID 1886862 reaction equation
Cl[CH:2]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH:3]=[O:4].[O:15]=[C:16](/[CH:22]=[CH:23]/[C:24]1[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=1)[C:17]([O:19][CH2:20][CH3:21])=[O:18]>C(Cl)(Cl)Cl>[CH2:5]([C@@H:2]1[C:3](=[O:4])[O:15][C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:22][C@@H:23]1[C:24]1[CH:25]=[CH:26][C:27]([CH3:30])=[CH:28][CH:29]=1)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

4

Reactant 2

HCID 108786402-chlorododecanalHCID 59445892HCID 59445892, compound

Product 1

HCID 86644267HCID 86644267, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Prepared according to the general procedure from 2-chlorododecanal and (E)-ethyl 2-oxo-4-p-tolylbut-3-enoate using 2 mol % 1 as the catalyst in 70% yield as a single diastereomer (colorless oil). [α]D20 (c 1.31, CHCl3)=+154.3; 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=6.5 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 169.2, 160.8, 142.3, 138.1, 133.1, 130.0, 128.1, 118.6, 62.1, 43.6, 41.2, 32.1, 29.7, 29.7, 29.5, 27.3, 26.4, 22.9, 21.3, 14.4, 14.3; IR (thin film) ν 3027, 2925, 2854, 1777, 1739, 1659, 1464, 1370, 1316, 1260, 1104 cm−1; HRMS (EI) calcd for C25H36O4 [M]+ 400.2614, found 400.2613; 99% ee (4S,5S)-isomer as determined by HPLC(OD-H, 20:1 hexanes/i-PrOH), tr (4S,5S)=8.0 min, tr (4R,5R)=9.2 min.

Workup

  1. customPrepared
  2. customtr (4S,5S)=8.0 min, tr (4R,5R)=9.2 min.

Sources & evidence

ORD record
ord-c5aff2c867554b438286577d19885c4a
Source dataset
uspto-grants-2013_08
Patent number
US08501658B2

Reaction notes

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