Sodium borohydride → HCID 10495522, compound

HRID 1872853Notes

Reaction equation

HRID 1872853 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][CH:10]=[C:11]([CH3:13])[CH3:12])=[C:4]([C:14]([CH3:17])([CH3:16])[CH3:15])[CH:3]=1.[BH4-].[Na+].C1C[O:23]CC1.O>C1COCC1.[OH-].[Na+].[Hg](OC(C)=O)OC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][CH2:10][C:11]([OH:23])([CH3:12])[CH3:13])=[C:4]([C:14]([CH3:17])([CH3:16])[CH3:15])[CH:3]=1

Participants

7

Reactant 3

HCID 4311764Sodium borohydrideHCID 10518096HCID 10518096, compoundHCID 21881883Oxolane--water (1/1)

Product 1

HCID 10495522HCID 10495522, compoundYield 67%

Reagents, catalysts & solvents 3

HCID 16683746DiacetyloxymercuryCatalystHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent2×

Procedure

To a yellow suspension of Hg(OAc)2 (6.36 g, 19.94 mmol, 1.0 equiv) in THF/water (25 mL/ 30 mL) is added 4-bromo-2-tert-butyl-1-(3-methyl-2-butenyloxy)benzene (5.93 g, 19.94 mmol) in THF (5 mL) dropwise and stirred at room temperature for 4 h. To the resulting pale yellow solution is added NaOH (15 mL, 3M) followed by NaBH4 (0.75 g, 19.94 mmol, 1.0 equiv) in NaOH (5 mL, 3M). The resulting ash colored suspension is stirred at room temperature for 30 min, diluted with hexanes, and washed with water, saturated aq. NH4Cl and brine. The aqueous layers are extracted with hexanes; the combined organic layers are dried (MgSO4), filtered and concentrated. The residue is purified by flash column chromatography on silica (hexanes/EtOAc; 101->311) to give the title compound (4.21 g, 67%) as an oil.

Workup

  1. stirringThe resulting ash colored suspension is stirred at room temperature for 30 min
  2. washwashed with water, saturated aq. NH4Cl and brine
  3. extractionThe aqueous layers are extracted with hexanes
  4. dry with materialthe combined organic layers are dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue is purified by flash column chromatography on silica (hexanes/EtOAc; 101->311)

Sources & evidence

ORD record
ord-bd849d83ef874eff91baea8e44c53a1c
Source dataset
uspto-grants-2000_08
Patent number
US06110960

Reaction notes

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