Hydrochloric Acid → HCID 22111430, compound

HRID 565588Notes

Reaction equation

HRID 565588 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C:15]3([C:20]#[CH:21])[CH2:18][C:17](=[O:19])[CH2:16]3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.[BH4-].[Li+].[Cl-].[NH4+].Cl>O1CCCC1>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C:15]3([C:20]#[CH:21])[CH2:18][CH:17]([OH:19])[CH2:16]3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 4148881Lithium borohydrideHCID 15480781HCID 15480781, compound

Product 1

HCID 22111430HCID 22111430, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-(3-cyclopentyloxy-4-methoxyphenyl)-3-ethynylcyclobutan-1-one (0.50 g, 1.76 mmol) (prepared in example 2b) in tetrahydrofuran (10 mL) at −30-40° C. under an argon atmosphere was added over 15 min a slurry of lithium borohydride (0.12 g, 5.28 mmol) in tetrahydrofuran (16 mL). The reaction was stirred 0.5 h and was poured into 0° C. ammonium chloride. 10% Hydrochloric acid was used to adjust to pH 3-4, the mixture was warmed to room temperature and was extracted with three portions of diethyl ether. The organic extract was dried (magnesium sulfate) and was evaporated. Purification by flash chromatography, eluting with 2:8 ethyl acetate : hexanes provided product as a colorless oil (0.54 g, 100%). 1H-NMR indicated the cis: trans isomer ratio to be ˜85:15.

Workup

  1. extractionwas extracted with three portions of diethyl ether
  2. extractionThe organic extract
  3. dry with materialwas dried (magnesium sulfate)
  4. customwas evaporated
  5. customPurification by flash chromatography
  6. washeluting with 2:8 ethyl acetate

Sources & evidence

ORD record
ord-bfce5075235c4b89b7179193b986f1d8
Source dataset
uspto-grants-2001_01
Patent number
US06172118B2

Reaction notes

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