Water → (7-Fluoro-2,3-dihydro-1,4-benzodioxine-5-yl)methanol

HRID 253297Notes

Reaction equation

HRID 253297 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:12](OC)=[O:13])[C:5]2[O:10][CH2:9][CH2:8][O:7][C:6]=2[CH:11]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[F:1][C:2]1[CH:3]=[C:4]([CH2:12][OH:13])[C:5]2[O:10][CH2:9][CH2:8][O:7][C:6]=2[CH:11]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 49780160Methyl 7-fluoro-2,3-dihydro-1,4-benzodioxine-5-carboxylate

Product 1

HCID 66891450(7-Fluoro-2,3-dihydro-1,4-benzodioxine-5-yl)methanolYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 7-fluoro-2,3-dihydro-1,4-benzodioxine-5-carboxylate (400 mg, 1.88 mmol) in tetrahydrofuran (20 mL) was cooled to 0° C. and then added lithium aluminum hydride (3.78 mL, 1.0 M solution in tetrahydrofuran). The reaction mixture was allowed to warm to room temperature and stirred for 45 min, at which time water (143 μL) was added followed by 15% sodium hydroxide (143 μL) and then water (286 μL) again. The white precipitate was filtered and the filtrate was concentrated to give 345 mg (100%) of (7-fluoro-2,3-dihydro-1,4-benzodioxine-5-yl)methanol as a colorless oil: 1H NMR (400 MHz, CDCl3): 6.63 (dd, J=2.8, 8.8 Hz, 1H), 6.56 (dd, J=3.2, 9.2 Hz, 1H), 4.64 (d, J=6.4 Hz, 2H), 4.28-4.25 (m, 4H).

Workup

  1. additionwas added
  2. filtrationThe white precipitate was filtered
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-bcc5e22d09ea44309364b0e3c64cfd25
Source dataset
uspto-grants-2011_01
Patent number
US07872014B2

Reaction notes

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