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

HRID 9296

반응식

HRID 9296 반응식
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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-02c6ad70fe5f4ce699d15439da78968c
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091232B2

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