Borane → HCID 18182599, compound

HRID 1359595Notes

Reaction equation

HRID 1359595 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH2:8][CH:7]([CH2:10][C:11](O)=[O:12])[C:6]=2[CH:14]=1.B>C1COCC1>[OH:12][CH2:11][CH2:10][CH:7]1[C:6]2[CH:14]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=2[O:9][CH2:8]1

Participants

4

Reactant 2

HCID 6331BoraneHCID 18182603HCID 18182603, compound

Product 1

HCID 18182599HCID 18182599, compoundYield 58.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 5-bromo-3-(carboxymethyl)-2,3-dihydro-benzofuran (reference example 15, 1.86 g , 7.68 mmol) in THF (21 mL) is cooled to 0° C. then a solution of borane in THF (7.7 mL, 1 M). On complete addition the cold bath is removed and stirring continued for 12 h. The reaction is quenched with aq. HCl (2M) diluted with ethyl acetate washed with sat. NaHCO3 solution then brine, dried over MgSO4 and concentrated. The residue is purified by flash chromatography (30% ethyl acetate in hexanes) to give the title compound (1.1 g) as an oil. 1H NMR (CDCl3) d 1.55 (bs, 1H), 1.88 (m, 1H), 2.03 (m, 1H), 3.61 (m, 1H), 3.75 (t, J=6 Hz, 2H), 4.29 (dd, J=8, 7 Hz, 1H), 4.68 (t, J=8 Hz, 1H), 6.68 (d, J=8 Hz, 1H), 7.22 (dd, J=8, 1 Hz, 1H), 7.28 (d, J=1 Hz, 1H). MS m/z242/244 Br pattern (M+).

Workup

  1. additionOn complete addition the cold bath
  2. customis removed
  3. customThe reaction is quenched with aq. HCl (2M)
  4. additiondiluted with ethyl acetate
  5. washwashed with sat. NaHCO3 solution
  6. dry with materialbrine, dried over MgSO4
  7. concentrationconcentrated
  8. customThe residue is purified by flash chromatography (30% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-d1151c7c9ff64c068ce5ef2e55125083
Source dataset
uspto-grants-2003_07
Patent number
US06599918B2

Reaction notes

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