Toluene → HCID 69792999, compound

HRID 984952Notes

Reaction equation

HRID 984952 reaction equation
CC(C[AlH]CC(C)C)C.C1(C)C=CC=CC=1.COC(=O)CC1C=CC([O:27][CH2:28]/[CH:29]=[C:30](/[C:32]2[CH:44]=[CH:43][C:42]3[C:41]4[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=4)[CH2:35][C:34]=3[CH:33]=2)\[CH3:31])=CC=1>C1COCC1>[CH:33]1[C:34]2[CH2:35][C:36]3[C:41](=[CH:40][CH:39]=[CH:38][CH:37]=3)[C:42]=2[CH:43]=[CH:44][C:32]=1/[C:30](/[CH3:31])=[CH:29]/[CH2:28][OH:27]

Participants

5

Reactant 3

HCID 1140TolueneHCID 14487Diisobutylaluminum hydrideHCID 10178071HCID 10178071, compound

Product 1

HCID 69792999HCID 69792999, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 1M solution of DIBAL-H in toluene (15 ml, 15 mmol) was added dropwise, at −70° C. over 30 min, to a stirred solution of (E)-{4-[3-(9H-fluoren-2-yl)-but-2-enyloxy]-phenyl}-acetic acid methyl ester (2.0 g, 7.2 mmol) in dry THF (100 ml) and stirred for 30 min. The mixture was warmed to room temperature, and stirred for 1.5 h. The mixture quenched with methanol (2 mL), added 1N HCl (30 ml) and the product extracted with ethyl acetate (3×50 ml). The combined organic extracts were washed with brine, dried (MgSO4), and evaporated to give the crude (E)-3-(9H-fluoren-2-yl)-but-2-en-1-ol.

Workup

  1. stirringstirred for 1.5 h
  2. customThe mixture quenched with methanol (2 mL)
  3. additionadded 1N HCl (30 ml)
  4. extractionthe product extracted with ethyl acetate (3×50 ml)
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried (MgSO4)
  7. customevaporated

Sources & evidence

ORD record
ord-88c5a54440a648e3a5ef615621468318
Source dataset
uspto-grants-2005_03
Patent number
US06869967B2

Reaction notes

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