Lithium borohydride → HCID 10715906, compound

HRID 1358867Notes

Reaction equation

HRID 1358867 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][C:16]([I:19])=[CH:15][CH:14]=2)=[C:9]1[CH:20]=[O:21])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li+].[BH4-]>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH:12]=[CH:11][C:10]([C:13]2[CH:14]=[CH:15][C:16]([I:19])=[CH:17][CH:18]=2)=[C:9]1[CH2:20][OH:21])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 10786964HCID 10786964, compound

Product 1

HCID 10715906HCID 10715906, compoundYield 82.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 6 (400 mg, 1.0 mmol) in anhydrous THF (12 mL) under argon was cooled to −20 to −25° C. and LiBH4 (55 mg, 2.5 mmol) was added in portions. The reaction was monitored by TLC (silica, hexanes/ethyl acetate (4:1)), and when no starting material was detected (20-25 min), the reaction was quenched with cold water (30 mL). The aqueous layer was extracted with CH2Cl2 and the organic layer was dried (Na2SO4), concentrated, and purified by flash column chromatography [silica; hexanes/ethyl acetate containing 1% Et3N (3:1)] yielding a gum (330 mg, 82%). 1H NMR δ1.62 (s, 9H), 3.61 (br, 1H), 4.66 (d, J=7.2 Hz, 2H), 6.25 (d, J=3.6 Hz, 1H), 7.18 (d, J=8.1 Hz, 2H), 7.22 (d, J=3.6 Hz, 1H), 7.71 (d, J=8.1 Hz, 2H); 13C NMR δ27.8, 55.3, 84.7, 92.4, 111.2, 121.3, 127.9, 130.0, 130.4, 134.1, 137.5, 149.8; FAB-MS obsd 399.0336, calcd 399.0331 (C16H18INO3).

Workup

  1. custom(20-25 min)
  2. customthe reaction was quenched with cold water (30 mL)
  3. extractionThe aqueous layer was extracted with CH2Cl2
  4. dry with materialthe organic layer was dried (Na2SO4)
  5. concentrationconcentrated
  6. custompurified by flash column chromatography [silica; hexanes/ethyl acetate containing 1% Et3N (3:1)]

Sources & evidence

ORD record
ord-d93a1796129142e18d15316f80603e35
Source dataset
uspto-grants-2003_07
Patent number
US06596935B2

Reaction notes

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