Methanol → (R)-1-(3-nitrophenyl)ethanol

HRID 2300888Notes

Reaction equation

HRID 2300888 reaction equation
CB1N2CCC[C@H]2C(C2C=CC=CC=2)(C2C=CC=CC=2)O1.B.[CH3:23][C:24]([C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([N+:32]([O-:34])=[O:33])[CH:27]=1)=[O:25].CO>C(Cl)Cl>[N+:32]([C:28]1[CH:27]=[C:26]([C@H:24]([OH:25])[CH3:23])[CH:31]=[CH:30][CH:29]=1)([O-:34])=[O:33]

Participants

5

Reactant 3

HCID 887MethanolHCID 8494m-NitroacetophenoneHCID 178419160HCID 178419160, compound

Product 1

HCID 11147933(R)-1-(3-nitrophenyl)ethanolYield 96.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (S)-tetrahydro-1-methyl-3,3-diphenyl-1H,3H-pyrrolo[1,2-c]- [1,3,2]-oxazaborole-borane (6.06 mmol) in CH2Cl2 (6 mL) at −20° C. was added a solution of 3-nitroacetophenone (6.06 mmol) in CH2Cl2 (6 mL) in a dropwise fashion over 30 min. The resulting mixture was stirred 45 min. longer then poured into cold methanol (−20° C.), and this mixture allowed to stir overnight while warming to room temperature. The mixture was then concentrated in vacuo then more methanol (100 mL) added and concentrated, and then added another 100 mL methanol and concentrated. The resulting crude was purified on silica gel in 60:40 hexanes:ethyl acetate to yield 0.98 g of the title compound. 1H NMR (500 MHz, CDCl3): δ 8.22 (m, 1H); 8.08 (m, 1H); 7.69 (d, J=7.8 Hz, 1H); 7.50 (t, J=7.8 Hz, 1H); 5.00 (m, 1H); 2.62 (s, 1H); 1.53 (d, J=7.1 Hz, 3H).

Workup

  1. stirringto stir overnight
  2. concentrationThe mixture was then concentrated in vacuo
  3. additionmore methanol (100 mL) added
  4. concentrationconcentrated
  5. additionadded another 100 mL methanol
  6. concentrationconcentrated
  7. customThe resulting crude was purified on silica gel in 60:40 hexanes

Sources & evidence

ORD record
ord-17012c13bdda464bba5b0f8e71c0433a
Source dataset
uspto-grants-2002_12
Patent number
US06498165B1

Reaction notes

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