3-Chloropropiophenone → HCID 10214453, compound

HRID 432064Notes

Reaction equation

[CH2:1]([Zn]CC)[CH3:2].[Cl:6][CH2:7][CH2:8][C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:10]>>[Cl:6][CH2:7][CH2:8][C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([OH:10])[CH2:1][CH3:2]

Participants

Reactant 2

HCID 702953-Chloropropiophenone

HCID 178418750HCID 178418750, compound

Product 1

HCID 10214453HCID 10214453, compoundYield 82%

Procedure

Diethylzinc addition to 3-chloropropiophenone (0.5 g, 2.97 mmol) was performed according to general procedure B using 10 mol % of Compound B (162.1 mg). The crude product was filtered through a pad of basic alumina with EtOAc (200 mL) to yield 485 mg of 8 (82% yield, 88% ee) as a colorless oil: [α]D 20=−21.0 (c 3.0, MeOH); 1H NMR (CDCl3, 360 MHz) δ 0.76 (dd, J=7.6, 7.6 Hz, 3H), 1.76-1.90 (m, 2H), 2.25-2.34 (m, 2H), 3.20-3.29 (m, 1H), 3.48-3.60 (m, 1H), 7.20-7.39 (m, 5H) ppm; 13C{1H} NMR (CDCl3, 90 MHz) δ 7.55, 36.08, 40.58, 45.46, 77.00, 125.20, 126.92, 128.45, 144.33 ppm; IR (KBr) 3566, 3462, 3087, 3060, 3027, 2969, 2936, 2879, 1602, 1494, 1446, 1340, 1251, 1173, 1124, 1074, 1055, 1031, 1014, 989, 900, 762, 702, 611 cm-1; HRMS calcd for C11H14Cl (—OH)+: 181.0784, found 181.0789 (chlorine splitting pattern observed).

Workup

filtrationThe crude product was filtered through a pad of basic alumina with EtOAc (200 mL)

Sources & evidence

ORD record: ord-d427ea30f42649b9ad1cbe478ad83d88
Source dataset: uspto-grants-2003_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06660884B2

Reaction notes

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