Tetrahydrofuran → tert-butyl 4-[(1S)-1-hydroxyethyl]benzoate

HRID 80571Notes

Reaction equation

HRID 80571 reaction equation
[C:1]([C:4]1[CH:16]=[CH:15][C:7]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].O1CCCC1.B(Cl)([C@H]1[C@H](C)[C@@H]2C(C)(C)[C@@H](C2)C1)[C@H]1[C@H](C)[C@@H]2C(C)(C)[C@@H](C2)C1.N(CCO)CCO>CCCCCC>[OH:3][C@H:1]([C:4]1[CH:16]=[CH:15][C:7]([C:8]([O:10][C:11]([CH3:13])([CH3:12])[CH3:14])=[O:9])=[CH:6][CH:5]=1)[CH3:2]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8113DiethanolamineHCID 11131038Chlorobis((1R,2S,3R,5R)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-yl)boraneHCID 13844704tert-Butyl 4-acetylbenzoate

Product 1

HCID 70815081tert-butyl 4-[(1S)-1-hydroxyethyl]benzoateYield 103.3%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To tert-butyl 4-acetylbenzoate (3.33 g) in a tetrahydrofuran (23 ml) solution, (−)-B-chlorodiisopinocampheylborane in a 65% hexane solution (11.2 ml) was added dropwise under ice cooling, then the mixture was stirred at that temperature for 1.5 hours. The reaction solution was concentrated, and the residue was diluted by diethyl ether. To the thus solution obtained, diethanolamine (4.3 ml) was added under ice cooling, and the mixture was stirred at room temperature for 2 hours. The precipitates were removed by filtration, and the filtrate was concentrated. The residue was purified by flash column chromatography (silica gel, hexane/ethyl acetate=9/1 to 4/1) to obtain the title compound (3.47 g).

Workup

  1. concentrationThe reaction solution was concentrated
  2. additionthe residue was diluted by diethyl ether
  3. customTo the thus solution obtained
  4. stirringthe mixture was stirred at room temperature for 2 hours
  5. customThe precipitates were removed by filtration
  6. concentrationthe filtrate was concentrated
  7. customThe residue was purified by flash column chromatography (silica gel, hexane/ethyl acetate=9/1 to 4/1)

Sources & evidence

ORD record
ord-1a363a750112412691c011c2365672b9
Source dataset
uspto-grants-2014_09
Patent number
US08846660B2

Reaction notes

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