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

반응식

HRID 65462 반응식
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]

참가 물질

4

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-4febf2555cbb4d9ba4b4ee53cca4bd48
출처 데이터셋
uspto-grants-1986_09
특허 번호
US04614747

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