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

HRID 705701Notes

Reaction equation

HRID 705701 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)methanolYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 7-chloro-1,3-benzodioxole-5-carbaldehyde (35.0 g, 0.19 mol) in THF (300 mL) was added NaBH4 (14.5 g, 0.38 mol) 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 (3×150 mL). The combined extracts were dried over Na2SO4 and evaporated under reduced pressure to afford the title compound (34.5 g; 98%), which was directly used in the next step.

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous phase was extracted with EtOAc (3×150 mL)
  3. dry with materialThe combined extracts were dried over Na2SO4
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-b221d46d58a043eb92d8c29b0269528b
Source dataset
uspto-grants-2015_11
Patent number
US09174967B2

Reaction notes

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