Ammonium Chloride → 6-Methoxy-2-p-methoxyphenyl-2-methyl-1-(6-tetrahydropyranyloxyhex-1-ynyl)-1,2,3,4-tetrahydronaphth-1-ol

HRID 1200091ノート

反応式

HRID 1200091 の反応式
C([Li])CCC.[O:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH:7]1[O:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]#[CH:18].[CH3:19][O:20][C:21]1[CH:22]=[C:23]2[C:28](=[CH:29][CH:30]=1)[C:27](=[O:31])[C:26]([C:33]1[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][CH:34]=1)([CH3:32])[CH2:25][CH2:24]2.[Cl-].[NH4+]>CCCCCC.O1CCCC1>[CH3:19][O:20][C:21]1[CH:22]=[C:23]2[C:28](=[CH:29][CH:30]=1)[C:27]([C:18]#[C:17][CH2:16][CH2:15][CH2:14][CH2:13][O:12][CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11][O:6]1)([OH:31])[C:26]([C:33]1[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][CH:34]=1)([CH3:32])[CH2:25][CH2:24]2

参加物

7

反応物 4

HCID 25517Ammonium ChlorideHCID 2821772-(Hex-5-yn-1-yloxy)tetrahydro-2h-pyranHCID 134065446-Methoxy-2-(4-methoxyphenyl)-2-methyltetraloneHCID 178418339Butyllithium

生成物 1

HCID 198307706-Methoxy-2-p-methoxyphenyl-2-methyl-1-(6-tetrahydropyranyloxyhex-1-ynyl)-1,2,3,4-tetrahydronaphth-1-ol

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

実験手順

n-Butyllithium (8.4 ml. of a 1.55 molar solution in hexane) was added to a solution of 6-tetrahydropyranyloxyhex-1-yne (2.25 g.) in tetrahydrofuran (25 ml.) at 10° C., the mixture was allowed to warm up to laboratory temperature and was stirred at that temperature for 30 minutes, and was then recooled to 10° C. A solution of 3,4-dihydro-6-methoxy-2-p-methoxyphenyl-2-methylnaphthalen-1(2H)-one (2.0 g.) in tetrahydrofuran (20 ml.) was added dropwise and the mixture was allowed to warm up to laboratory temperature and stirred at that temperature for 30 minutes. Saturated aqueous ammonium chloride solution (50 ml.) was added and the mixture was extracted with ethyl acetate. The extract was dried and evaporated to dryness and the residue was purified by chromatography on a silica gel column using a 3:1 v/v mixture of petroleum ether (b.p. 60°-80° C.) and ethyl acetate as eluant. The product was crystallised from ethanol and there was thus obtained, as a mixture of isomers, 6-methoxy-2-p-methoxyphenyl-2-methyl-1-(6-tetrahydropyranyloxyhex-1-ynyl)-1,2,3,4-tetrahydronaphth-1-ol, m.p. 80°-82° C.

後処理

  1. temperatureto warm up to laboratory temperature
  2. customwas then recooled to 10° C
  3. temperatureto warm up to laboratory temperature
  4. stirringstirred at that temperature for 30 minutes
  5. extractionthe mixture was extracted with ethyl acetate
  6. customThe extract was dried
  7. customevaporated to dryness
  8. customthe residue was purified by chromatography on a silica gel column
  9. additiona 3:1 v/v mixture of petroleum ether (b.p. 60°-80° C.) and ethyl acetate as eluant
  10. customThe product was crystallised from ethanol and there

出典と根拠

ORDレコード
ord-b5526fe13eae4148b7555390772b7fbd
出典データセット
uspto-grants-1990_02
特許番号
US04904661

反応ノート

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