1-Methyl-2-(1-methylethenyl)cyclobutaneethanol → HCID 15225559, 화합물

HRID 861205노트

반응식

HRID 861205 반응식
[CH3:1][C:2]1([CH2:9][CH2:10][OH:11])[CH2:5][CH2:4][CH:3]1[C:6]([CH3:8])=[CH2:7].CC1(CC=[O:22])CCC1C(C)=C.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>>[CH3:1][C:2]1([CH2:9][C:10]([OH:22])=[O:11])[CH2:5][CH2:4][CH:3]1[C:6]([CH3:8])=[CH2:7]

참가 물질

4

반응물 3

HCID 1173141-Methyl-2-(1-methylethenyl)cyclobutaneethanolHCID 15225560HCID 15225560, 화합물HCID 178418287HCID 178418287, 화합물

생성물 1

HCID 15225559HCID 15225559, 화합물

실험 절차

A four gram sample of racemic 1-methyl-2-(1-methylethenyl)-cyclobutaneethanol (grandisol I) [2] (Bedoukian, Inc.) was oxidized to the corresponding racemic aldehyde, 1-methyl-2-(1-methylethenyl)-cyclobutaneacetaldehyde (grandisal) using pyridinium chlorochromate (Webster) (3.4 g, % yield 86.1). The racemic aldehyde was distilled under vacuum and a 3 gram sample was subsequently oxidized to racemic 1 using AgNO3 and NaOH (Pickett): nearly colorless oil (1.23 g, % yield 32.2); eims m/z (rel. int. %) 168 (1), 125 (12), 109 (14), 108 (35), 93 (9), 91 (3), 81 (6), 79 (11), 77 (10), 69 (11), 68 (100), 67 (86), 55 (11), 53 (30), 43 (35), 41 (41); H NMR (CDCl3) δ 2.61 (1H, m, H-2), 1.83 (1H, m, H-3a), 1.95 (1H, m, H-3b), 1.71 (1H, m, H-4a), 1.95 (1H, m, H-4b), 1.31 (3H, s, Me-5), 2.03 (1H, dd, J=14.6,H-6a), 2.54 (1H, d, J=14.6, H-6b), 4.85 (1H, m, H-9a), 4.65 (1H, m, H-9b), 1.64 (3H, s, Me-10); 13C NMR (CDCl3) δ 41.1 (C-1), 51.9 (C-2), 18.7 (C-3), 29.0 (C-4), 27.9 (C-5), 38.5 (C-6), 179.7 (C-7), 144.1 (C-8), 110.3 (C-9), 22.8 (C-10).

후처리

  1. distillationThe racemic aldehyde was distilled under vacuum

출처 및 근거

ORD 기록
ord-b31c2d235bb74fa4bbf6c7138e3a8877
출처 데이터셋
uspto-grants-1998_02
특허 번호
US05714139

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