Chloroform → 4-Phenyl-2-butanol

HRID 1419604Notes

Reaction equation

HRID 1419604 reaction equation
C([O:4][C:5]([CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[CH2:6])(=O)C.[H][H].C(OC(CCC1C=CC=CC=1)C)(=O)C.C(Cl)(Cl)Cl>C1COCC1.F[B-](F)(F)F.C1([Rh+]C2CCCCC=CC=2)CCCCC=CC=1>[C:9]1([CH2:8][CH2:7][CH:5]([OH:4])[CH3:6])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 6212ChloroformHCID 615171-Phenyl-3-acetoxybutane2×HCID 158644694-Phenylbut-1-en-2-yl acetateHCID 178418361HCID 178418361, compound

Product 1

HCID 613024-Phenyl-2-butanol

Reagents, catalysts & solvents 2

HCID 178420271HCID 178420271, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

This reaction was performed as in Example 1 with bis(cyclooctadienyl)rhodium tetrafluoroborate (20 mg; 0.05 mmol; 0.02 equiv), R,R-1,2-bis(2,5-dimethylphospholano)benzene (6, R"=CH3 ; 18 mg; 0.06 mmol; 0.024 equiv) and 4-phenylbut-1-en-2-yl acetate (476 mg; 2.5 mmol) in 20 mL of degassed THF until hydrogen uptake ceased (1.5 h) to afford 0.51 g of crude product. 1H NMR analysis indicated 4-phenyl-2-butyl acetate as the sole product, and chiral GC analysis and comparison to racemate indicated 77% ee for 4-phenyl-2-butyl acetate. Base hydrolysis afforded 4-phenyl-2-butanol, [α]D25 -12.0° (c 2.115, CHCl3), which indicates the (R) configuration when compared with the known rotation ([α]D +13.5° (c 2.1, CHCl3)) for the (S) enantiomer.

Workup

  1. custom(1.5 h)
  2. customto afford 0.51 g of crude product
  3. customBase hydrolysis

Sources & evidence

ORD record
ord-9fac468dc4eb48768975a353cac190d4
Source dataset
uspto-grants-1999_03
Patent number
US05886214

Reaction notes

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