Diisobutylaluminum hydride → [2-(3-Methyl-cyclohex-3-enyl)ethoxymethyl]-benzene

HRID 9296

反応式

HRID 9296 の反応式
CO[C:3]([C:5]1[CH2:10][CH:9]([CH2:11][CH2:12][O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:8][CH2:7][CH:6]=1)=O.CC(C[AlH]CC(C)C)C.N1C=CC=CC=1.S(=O)(=O)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:3][C:5]1[CH2:10][CH:9]([CH2:11][CH2:12][O:13][CH2:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:8][CH2:7][CH:6]=1

参加物

6

反応物 4

HCID 14487Diisobutylaluminum hydrideHCID 168533Sulfur trioxide-pyridineHCID 21226445Aluminium lithium hydrideHCID 235495385-(2-Benzyloxy-ethyl)-cyclohex-1-enecarboxylic acid methyl ester

生成物 1

HCID 21986115[2-(3-Methyl-cyclohex-3-enyl)ethoxymethyl]-benzene収率 82%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

5-(2-Benzyloxy-ethyl)-cyclohex-1-enecarboxylic acid methyl ester (Intermediate R3 obtained above in Example R1 in accordance with Method R) was reduced with DIBAL. The resulting alcohol (Intermediate R7, 1.18 g, 4.81 mmol) in THF (20 mL) at 0° C. was treated with sulfur trioxide-pyridine. (1.15 g, 7.21 mmol) for 3 h. LiAlH4 (15 mL, 15 mmol) was injected into the mixture at 0° C. The solution was allowed to warm to rt for 18 h. The mixture was subjected to an aqueous work-up and purified by chromatography to give [2-(3-methyl-cyclohex-3-enyl)-ethoxymethyl]-benzene (Intermediate R8, 0.90 g, 82%). Deprotection with Na/NH3 and subsequent “Swern” oxidation produced (3-methyl-cyclohex-3-enyl)-acetaldehyde (Intermediate R9). (3-methyl-cyclohex-3-enyl)-acetaldehyde (Intermediate R9) was subjected to the applicable steps combined from Method A and Method P to yield 4-(3-methyl-cyclohex-3-enylmethyl)-1,3-dihydro-imidazol-2-one (Compound 57).

後処理

  1. customwas injected into the mixture at 0° C
  2. custompurified by chromatography

出典と根拠

ORDレコード
ord-02c6ad70fe5f4ce699d15439da78968c
出典データセット
uspto-grants-2006_08
特許番号
US07091232B2

関連ノート

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