Aluminium lithium hydride → 2,5,9-Trimethyl-11-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8,10-undecapentaene-1-ol

HRID 65462

反応式

HRID 65462 の反応式
C([O:3][C:4](=O)[C:5]([CH3:26])=[CH:6][CH:7]=[C:8]([CH3:25])[CH:9]=[CH:10][CH:11]=[C:12]([CH3:24])[CH:13]=[CH:14][C:15]1[C:20]([CH3:22])([CH3:21])[CH2:19][CH2:18][CH2:17][C:16]=1[CH3:23])C.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:26][C:5](=[CH:6][CH:7]=[C:8]([CH3:25])[CH:9]=[CH:10][CH:11]=[C:12]([CH3:24])[CH:13]=[CH:14][C:15]1[C:20]([CH3:22])([CH3:21])[CH2:19][CH2:18][CH2:17][C:16]=1[CH3:23])[CH2:4][OH:3]

参加物

4

反応物 2

HCID 21226445Aluminium lithium hydrideHCID 541525652,5,9-Trimethyl-11-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8,10-undecapentaenoic acid ethyl ester

生成物 1

HCID 537496932,5,9-Trimethyl-11-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8,10-undecapentaene-1-ol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 2,5,9-trimethyl-11-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8,10-undecapentaenoic acid ethyl ester (1.85 g, 5 mmol) in 25 ml of anhydrous THF is cooled to -10° C. and 0.19 g (5 mmol) of LAH is added in portions. The resulting mixture is stirred for 4 hours and quenched carefully with 0.4 ml of water. The mixture is suction-filtered and the residue thoroughly washed with ether. The combined filtrate and washings are dried (MgSO4) and evaporated under reduced pressure to give the crude product. Purification by HPLC (4% ethylacetate in hexane on silica gel column) gives the pure desired product.

後処理

  1. customquenched carefully with 0.4 ml of water
  2. filtrationThe mixture is suction-filtered
  3. washthe residue thoroughly washed with ether
  4. dry with materialThe combined filtrate and washings are dried (MgSO4)
  5. customevaporated under reduced pressure
  6. customto give the crude product
  7. customPurification by HPLC (4% ethylacetate in hexane on silica gel column)

出典と根拠

ORDレコード
ord-4febf2555cbb4d9ba4b4ee53cca4bd48
出典データセット
uspto-grants-1986_09
特許番号
US04614747

関連ノート

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