Isopropanol hexane → HCID 58839423, compound

HRID 2219803Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:20])[C@@H:5]([OH:19])[CH2:6][C:7]([C:9]1[CH:18]=[CH:17][C:16]2[C:11](=CC=CC=2)[CH:10]=1)=[O:8])[CH3:2].[CH3:21][CH2:22]CCCC.CC(O)C>>[CH2:1]([O:3][C:4](=[O:20])[C@@H:5]([OH:19])[CH:6]([C:7](=[O:8])[C:9]1[CH:10]=[CH:11][CH:16]=[CH:17][CH:18]=1)[CH2:21][CH3:22])[CH3:2]

Participants

Reactant 2

HCID 21585144Isopropanol hexane

HCID 58839403HCID 58839403, compound2×

Product 1

HCID 58839423HCID 58839423, compound

Procedure

1H NMR syn (CDCl3) δ=0.93 (t, 3H, J=7.5 Hz), 1.19 (t, 3H, J=7.1 Hz), 1.70-2.05 (m, 2H), 3.18 (brs, 1H), 3.83 (dt, 1H, J=5.3, 8.3 Hz), 4.19 (q, 2H, J=7.1 Hz), 4.51 (d, 1H, J=5.3 Hz), 7.42-7.54 (m, 2H), 7.54-7.62 (m, 1H), 7.90-8.02 (m, 2H); anti (CDCl3) δ=1.04 (t, 3H, J=7.6 Hz), 1.15 (t, 3H, J=7.1 Hz), 1.80-1.95 (m, 2H), 3.70 (d, 1H, J=9.5 Hz), 3.83 (dt, 1H, J=4.2, 7.1 Hz), 4.09 (q, 2H, J=7.1 Hz), 4.43 (dd, 1H, J=4.2, 9.5 Hz), 7.46-7.52 (m, 2H), 7.56-7.63 (m, 1H), 7.88-7.95 (m, 2H); 13C NMR syn (CDCl3) δ=12.0, 13.9, 21.3, 51.2, 61.9, 71.1, 128.3, 128.6, 133.2, 137.0, 173.6, 201.5; anti(CDCl3) δ=12.0, 13.9, 22.3, 50.1, 61.4, 71.3, 128.3, 128.7, 133.5, 136.6, 173.4, 203.9; IR (neat) syn 3477, 2972, 2876, 1738, 1675, 1596, 1447, 1372, 1255, 1220, 1118, 1023, 931, 849, 779, 701; anti 3485, 3062, 2966, 2941, 2875, 1738, 1682, 1596, 1579, 1448, 1368, 1268, 1208, 1134, 1100, 1028, 914, 849, 785, 699 cm−1; HRMS (FAB); Exact mass calcd for C14H19O4 [M+H]+, 251.1283. Found 251.1277.; HPLC, Daicel Chiralcel AS, hexane/iPrOH=4/1, flow rate=0.5 mL/min: tR=13.7 min (2S, 3S), tR=15.3 min (2S, 3R), tR=17.6 min (2R, 3R), tR=23.1 min (2R, 3S).

Sources & evidence

ORD record: ord-d8d8285a305a452da26e95ef9b86994b
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07414145B2

Reaction notes

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