1-Methyl-2-(1-methylethenyl)cyclobutaneethanol → HCID 15225559、化合物

HRID 861205ノート

反応式

HRID 861205 の反応式
[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]

参加物

4

反応物 3

HCID 1173141-Methyl-2-(1-methylethenyl)cyclobutaneethanolHCID 15225560HCID 15225560、化合物HCID 178418287HCID 178418287、化合物

生成物 1

HCID 15225559HCID 15225559、化合物

実験手順

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).

後処理

  1. distillationThe racemic aldehyde was distilled under vacuum

出典と根拠

ORDレコード
ord-b31c2d235bb74fa4bbf6c7138e3a8877
出典データセット
uspto-grants-1998_02
特許番号
US05714139

反応ノート

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