Dimethyl L-tartrate → HCID 67848361, 화합물

HRID 1491569

반응식

HRID 1491569 반응식
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]

참가 물질

4

반응물 3

HCID 11851Dimethyl L-tartrateHCID 3018174[2-(Dimethoxymethyl)oct-1-en-1-yl]benzeneHCID 70235729HCID 70235729, 화합물

생성물 1

HCID 67848361HCID 67848361, 화합물

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-19c56d2abf284b378ec4373ae8e31276
출처 데이터셋
uspto-grants-1994_12
특허 번호
US05371069

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