Ammonium Chloride → (7-Chloro-1,3-dioxaindan-5-yl)methanol

HRID 1403845Notes

Reaction equation

HRID 1403845 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]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 6764927-Chloro-1,3-dioxaindane-5-carbaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 4962440(7-Chloro-1,3-dioxaindan-5-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 7-chlorobenzo[d][1,3]dioxole-5-carbaldehyde (6.0 g, 33 mmol) is THF (50 mL) was added NaBH4 (2.5 g, 64 mmol)) in portions 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

  1. customThe organic layer was separated
  2. extractionthe aqueous phase was extracted with EtOAc (50 mL×3)
  3. dry with materialThe combined extracts were dried over Na2SO4
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-86d4841f96e74dbe81a50930383a7d7a
Source dataset
uspto-grants-2014_12
Patent number
US08912199B2

Reaction notes

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