Dimethyl L-tartrate → HCID 67848361, compound

HRID 1885397

Reaction equation

COC(OC)C(CCCCCC)=CC1C=CC=CC=1.C([C@@H]([C@H](C(OC)=O)O)O)(OC)=O.[CH2:32](/[C:38](/[CH:46]1[O:50][C@@H:49]([C:51]([O:53][CH3:54])=[O:52])[C@H:48]([C:55]([O:57][CH3:58])=[O:56])[O:47]1)=[CH:39]/[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[CH2:33][CH2:34][CH2:35][CH2:36][CH3:37].[K+].[Br-]>>[CH2:32](/[C:38](/[CH:46]1[O:50][C@@H:49]([C:51]([O:53][CH3:54])=[O:52])[C@H:48]([C:55]([O:57][CH3:58])=[O:56])[O:47]1)=[CH:39]\[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]

Participants

Reactant 4

HCID 11851Dimethyl L-tartrate

HCID 253877Potassium Bromide

HCID 3018174[2-(Dimethoxymethyl)oct-1-en-1-yl]benzene

HCID 70235729HCID 70235729, compound

Product 1

HCID 67848361HCID 67848361, compound

Procedure

In a fashion similar to that described in Example 4, α-hexylcinnamaldehyde dimethyl acetal and dimethyl L-tartrate were condensed to provide a mixture of (E)-and (Z)-(4R,5R)-2-(1-hexyl-2-phenyl-1-ethenyl)-4,5-dicarbomethoxy-1,3-dioxolane in an approximate ratio of 90:10 Crystallization provided the pure E-isomer, mp 49°-50° C., [α]D25 -2.2 (c, 0.2, methanol). 1H-NMR (CDCl3) δ7.35-7.26 (5H,m), 6.74 (1H,s), 5.84 (1H,s) 4.86 (1H, d, J=4.4 Hz), 4.70 (1H, d, J=4.4 Hz), 3.85 (3H,s), 3.80 (3H,s), 2.34-2.27 (2H,m), 1.58-1.55 (2H,m), 1.37-1.26 (6H,m), 0.93-0.87 (3H,m), IR (KBr) 2900, 2840, 1730, 1430, 1340, 1200, 1100, 1060, 1030, 980, 950, 915, 870, 790, 750, 730, 690 cm-1. MS m/e (% abundance) 305 (4), 292 (17), 291 (100), 145 (18), 142 (25), 131 (73), 129 (76), 128 (26), 117 (74), 116 (17), 115 (51), 104 (29), 91 (57), 59 (31), 41 (25).

Workup

customcondensed
customto provide
customin an approximate ratio of 90:10 Crystallization
customprovided the pure E-isomer, mp 49°-50° C., [α]D25 -2.2 (c, 0.2, methanol)

Sources & evidence

ORD record: ord-89f6414b6e6440adafa95df4711f3983
Source dataset: uspto-grants-1992_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05144048

Linked notes

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