Borane → HCID 57185796, compound

HRID 440348Notes

Reaction equation

HRID 440348 reaction equation
[CH:1]1[C:13]2[CH:12](CCCC(O)=O)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.B.[CH2:21]1[CH2:25][O:24][CH2:23][CH2:22]1>>[C:1]1([CH2:25][CH2:21][CH2:22][CH2:23][OH:24])[C:13]2[CH2:5][C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:12]=2[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 6331BoraneHCID 8028Tetrahydrofuran2×HCID 10422327HCID 10422327, compound

Product 1

HCID 57185796HCID 57185796, compoundYield 88%

Procedure

A solution of the acid material 6 (3.50 g; 13.90 mmol) in 30 mL of THF was cooled to 0° C. and treated with 13.90 mL of a 1.0M solution of borane in THF (13.90 mmol). The resulting mixture was stirred overnight, then quenched with saturated ammonium chloride (30 mL). The product was extracted into ethyl acetate, and the organic phase was washed successively with 3% HCl, saturated sodium bicarbonate, and brine. Removal of the solvent furnished the alcohol (2.90 g; 88%), which crystallized to a waxy solid on standing and did not require further purification. 1H NMR (CDCl3): δ 1.22 (m, 2H); 1.49 (m, 2H); 1.98 (m, 2H); 3.50 (t, 2H); 3.95 (t, 1H); 7.33 (m, 4H); 7.49 (d, 2H, J=7.3); 7.73 (d, 2H, J=7.3).

Workup

  1. customquenched with saturated ammonium chloride (30 mL)
  2. extractionThe product was extracted into ethyl acetate
  3. washthe organic phase was washed successively with 3% HCl, saturated sodium bicarbonate, and brine
  4. customRemoval of the solvent

Sources & evidence

ORD record
ord-99b93558f66d4fbd9ad2b0e774c74292
Source dataset
uspto-grants-1996_05
Patent number
US05519043

Reaction notes

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