Ammonium Chloride → (7-Chloro-1,3-dioxaindan-5-yl)methanol
Reaction equation
[Cl:1][C:2]1[C:7]2[O:8][CH2:9][O:10][C:6]=2[CH:5]=[C:4]([CH:11]=[O:12])[CH:3]=1.[BH4-].[Na+].[NH4+].[Cl-]>C1COCC1>[Cl:1][C:2]1[C:7]2[O:8][CH2:9][O:10][C:6]=2[CH:5]=[C:4]([CH2:11][OH:12])[CH:3]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 7-chlorobenzo[d][1,3]dioxole-5-carbaldehyde (6.0 g, 33 mmol) in THF (50 mL) was added NaBH4 (2.5 g, 64 mmol)) in portion at 0° C. The mixture was stirred at this temperature for 30 min and then poured into aqueous NH4Cl solution. The organic layer was separated, and the aqueous phase was extracted with EtOAc (50 mL×3). The combined extracts were dried over Na2SO4 and evaporated under reduced pressure to afford (7-chlorobenzo[d][1,3]dioxol-5-yl)methanol, which was directly used in the next step.
Workup
- customThe organic layer was separated
- extractionthe aqueous phase was extracted with EtOAc (50 mL×3)
- dry with materialThe combined extracts were dried over Na2SO4
- customevaporated under reduced pressure
Sources & evidence
- ORD record
- ord-6ffbf17a03144399ab6b2331ff3a80f0
- Source dataset
- uspto-grants-2013_09
- Patent number
- US08524767B2
Reaction notes
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