Tetrahydrofuran → HCID 68473560, compound

HRID 473072Notes

Reaction equation

HRID 473072 reaction equation
[CH3:1][C:2]1([CH2:16][O:17][Si:18]([CH2:23][CH3:24])([CH2:21][CH3:22])[CH2:19][CH3:20])[CH2:10][C:9]2[C:4](=[C:5]([CH3:14])[C:6]([CH:12]=[CH2:13])=[C:7]([CH3:11])[CH:8]=2)[CH:3]1[OH:15].B(C1CCCCC1)C1CCCCC1.C1C[O:41]CC1>>[OH:41][CH2:13][CH2:12][C:6]1[C:5]([CH3:14])=[C:4]2[C:9]([CH2:10][C:2]([CH3:1])([CH2:16][O:17][Si:18]([CH2:23][CH3:24])([CH2:21][CH3:22])[CH2:19][CH3:20])[CH:3]2[OH:15])=[CH:8][C:7]=1[CH3:11]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 15879360CID 15879360HCID 684751572,5,7-Trimethyl-2-triethylsilanyloxymethyl-6-vinyl-indan-1-ol

Product 1

HCID 68473560HCID 68473560, compoundYield 81%

Procedure

To the stirred solution of compound 8 (0.85 g, 2.45 mmol) in dry THF was added (Cy)2BH (0.87 g, 4.91 mmol) slowly at 0° C. under argon atmosphere. The reaction mixture was warmed to room temperature and stirred for 12 h. The reaction mixture was quenched with 2N NaOH (6 mL) and H2O2 (3 mL) at 0° C. and allowed to stir for 4 h. Then crude reaction mixture was extracted with ethyl acetate (40 mL), washed with water (10 mL), brine (10 mL) dried (Na2SO4) and concentrated in vacuo. Purification by column chromatography (SiO2, 8 to 10% EtOAc in petroleum ether eluant) gave pure compound 9 (0.72 g, 81%) as gummy syrup.

Workup

  1. customThe reaction mixture was quenched with 2N NaOH (6 mL) and H2O2 (3 mL) at 0° C.
  2. stirringto stir for 4 h
  3. customThen crude reaction mixture
  4. extractionwas extracted with ethyl acetate (40 mL)
  5. washwashed with water (10 mL), brine (10 mL)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. customPurification by column chromatography (SiO2, 8 to 10% EtOAc in petroleum ether eluant)

Sources & evidence

ORD record
ord-ffcdd68e47104200a9b3c4395ec2e520
Source dataset
uspto-grants-2014_01
Patent number
US08633252B2

Reaction notes

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