Methanol → HCID 19598047, compound

HRID 1657052Notes

Reaction equation

HRID 1657052 reaction equation
[C:1]1([C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][O:3]1)=[O:2].[H-].C([Al+]CC(C)C)C(C)C.[CH3:21][OH:22].O>C1(C)C=CC=CC=1>[OH:2][CH:1]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([O:22][CH3:21])[C:5]=2[CH2:4][O:3]1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 6885PhthalideHCID 21225700Diisobutylaluminumhydride2×

Product 1

HCID 19598047HCID 19598047, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
-78 °C

Procedure

The phthalide (346 mg) prepared in reference example 33 was dissolved in toluene (20 ml). The solution was cooled to -78° C. A 1.76N solution of diisobutylaluminum hydride (DIBAL) in toluene (1.43 ml) was added dropwise to the cooled solution. The mixture was stirred for 30 min. at -78° C. Methanol (0.2 ml) was added to the reaction solution to decompose the excess DIBAL. Water was added to the reaction solution. A temperature of the solution was up to room temperature. The solution was stirred for 30 min. at room temperature. The reaction solution was dried over anhydrous sodium sulfate, washed with ethyl acetate and evaporated to give the residue contained the title compound having the following physical data. The residue was used in next reaction without purification.

Workup

  1. customwas up to room temperature
  2. stirringThe solution was stirred for 30 min. at room temperature
  3. dry with materialThe reaction solution was dried over anhydrous sodium sulfate
  4. washwashed with ethyl acetate
  5. customevaporated
  6. customto give the residue

Sources & evidence

ORD record
ord-e626ec3ece6b47729d8c3c4bd12a491c
Source dataset
uspto-grants-1993_10
Patent number
US05256686

Reaction notes

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