Dimethyl L-tartrate → HCID 67848361、化合物

HRID 1491569

反応式

HRID 1491569 の反応式
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]>>[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]

参加物

4

反応物 3

HCID 11851Dimethyl L-tartrateHCID 3018174[2-(Dimethoxymethyl)oct-1-en-1-yl]benzeneHCID 70235729HCID 70235729、化合物

生成物 1

HCID 67848361HCID 67848361、化合物

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-19c56d2abf284b378ec4373ae8e31276
出典データセット
uspto-grants-1994_12
特許番号
US05371069

関連ノート

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