Acetic Acid → HCID 59910718, compound

HRID 249111Notes

Reaction equation

HRID 249111 reaction equation
C1C[O:37][C:3]([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])([CH2:4][CH2:5][C@H:6]2[C@H:10]([O:11]C3CCCCO3)[CH2:9][C:8](=[O:18])[C@@H:7]2[CH2:19]/[CH:20]=[CH:21]\[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27]([O-:29])=[O:28])O1.C(O)(=O)C.[CH2:43]1[CH2:47]OC[CH2:44]1>O>[OH:11][C@@H:10]1[CH2:9][C:8](=[O:18])[C@H:7]([CH2:19]/[CH:20]=[CH:21]\[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27]([O:29][CH:43]([CH3:47])[CH3:44])=[O:28])[C@H:6]1[CH2:5][CH2:4][C:3](=[O:37])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 8028TetrahydrofuranHCID 86746860HCID 86746860, compound

Product 1

HCID 59910718HCID 59910718, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The compound (45) (0.311 g) was dissolved in a mixed solvent (5 ml) consisting of acetic acid, THF and water (2:1:1) and kept at 50° C. for 3 hours. The resultant mixture was worked up with the conventional procedure and the residue was subjected to silicagel column chromatography to give the titled compound (46). Yield: 0.156 g (66%). Compound (46) [Q1 =Q2 =H, Rb-Rc=hexyl, P3 =isopropyl]NMR(CDCl3)δ: 0.86 (t,3H,J=6.5 Hz), 1.20 (d,6H,J=6 Hz), 1.23-2.75 (m,33H), 4.20 (m,1H), 4.99 (Hept,1H,J=6 Hz), 5.15-5.50 (m,2H)

Sources & evidence

ORD record
ord-9ed791447eee48cd9dbdbf6a7992740d
Source dataset
uspto-grants-1993_05
Patent number
US05212324

Reaction notes

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