Benzyl Alcohol → HCID 69211681, compound

HRID 902920Notes

Reaction equation

HRID 902920 reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.[CH3:14][O:15][C:16](=[O:50])[CH:17]([CH2:42][CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)[CH:18]([C:27](N1C(CC2C=CC=CC=2)COC1=O)=[O:28])[CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21]>C1COCC1>[CH3:14][O:15][C:16](=[O:50])[CH:17]([CH2:42][CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)[CH:18]([C:27]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:28])[CH2:19][C:20]([O:22][C:23]([CH3:25])([CH3:24])[CH3:26])=[O:21]

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 69211810HCID 69211810, compoundHCID 178418339Butyllithium

Product 1

HCID 69211681HCID 69211681, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-10 °C

Procedure

To a stirred solution of benzyl alcohol (0.5 mL, 4.41 mmol) in anhydrous THF (16 mL) at −70° C., was added n-butyl lithium (2.5 M, 1.4 mL, 3.53 mmol). After 10 minutes of stirring, the solution was transferred by means of a cannula to a solution of the compound of example 51 in anhydrous THF (15 mL) at −70° C. The reaction was allowed to warm to −10° C. over a period of 2 h, after which time, it was placed in an ice bath and stirred for another 50 minutes. Finally, the reaction was quenched by the addition of a saturated ammonium chloride solution. The mixture was extracted several times using ethyl acetate. The recombined organic layer was extracted with brine, dried over sodium sulfate, filtered and evaporated. The resultant crude was flashed using 10% ethyl acetate in hexanes to give the product as a colorless oil. 1H-NMR(CDCl3, 300 MHz: 1.39, 1.40(2s, 9H); 1.70(m, 1H); 2.01(m, 1H); 2.31-2.74(m, 4H); 2.83(m, 1H); 3.21(m, 1H); 3.61, 3.64(2s, 3H); 5.11(m, 2H); 7.08-7.35(m, 10H).

Workup

  1. customafter which time, it was placed in an ice bath
  2. stirringstirred for another 50 minutes
  3. customFinally, the reaction was quenched by the addition of a saturated ammonium chloride solution
  4. extractionThe mixture was extracted several times
  5. extractionThe recombined organic layer was extracted with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-d7a947eaf5814e82867ffe23973abd69
Source dataset
uspto-grants-2008_04
Patent number
US07365091B2

Reaction notes

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