Methanol → 2-(1,3-Dioxaindan-5-yl)ethan-1-ol

HRID 456586Notes

Reaction equation

HRID 456586 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][C:11](O)=[O:12])=[CH:9][C:4]=2[O:3][CH2:2]1.CO>O1CCCC1>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][CH2:11][OH:12])=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

4

Reactant 2

HCID 887MethanolHCID 76115Benzo-1,3-dioxole-5-acetic acid

Product 1

HCID 27598462-(1,3-Dioxaindan-5-yl)ethan-1-olYield 84.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of benzo[1,3]dioxol-5-yl-acetic acid (2.5 g, 13.9 mmol) in tetrahydrofuran (15 ml) under argon at −10° C. was treated dropwise with borane-dimethylsulfide complex (1.45 ml, 15.3 mmol). The mixture was stirred at ambient temperature for 1.5 hours (CAUTION—exothermic reaction). The orange solution was cooled to ˜5° C. (ice bath) and methanol (1.4 ml) was added. After 0.5 hour at room temperature, the mixture was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution. The organic extract was dried and evaporated to give a yellow oil (1.95 g, 84%).

Workup

  1. custom(CAUTION—exothermic reaction)
  2. additionwas added
  3. waitAfter 0.5 hour at room temperature
  4. customthe mixture was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution
  5. extractionThe organic extract
  6. customwas dried
  7. customevaporated

Sources & evidence

ORD record
ord-dadc8725412f43c9a0455c7f5e60521b
Source dataset
uspto-grants-2007_03
Patent number
US07186730B2

Reaction notes

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