Sodium cyanoborohydride → HCID 68840392, compound

HRID 1432601Notes

Reaction equation

HRID 1432601 reaction equation
[Br:1][C:2]1[S:6][C:5]([C:7]2(O)[CH2:12][CH2:11][O:10][CH2:9][CH2:8]2)=[CH:4][C:3]=1[CH3:14].C([BH3-])#N.[Na+]>[Zn+2].[I-].[I-].ClCCCl>[Br:1][C:2]1[S:6][C:5]([CH:7]2[CH2:12][CH2:11][O:10][CH2:9][CH2:8]2)=[CH:4][C:3]=1[CH3:14]

Participants

5

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 68842710HCID 68842710, compound

Product 1

HCID 68840392HCID 68840392, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 9883512zinc(II)iodideCatalystHCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 4-(5-bromo-4-methyl-thiophen-2-yl)-tetrahydro-pyran-4-ol (2.3 g, 8.30 mmol) and 1,2-dichloroethane (50 mL) is added ZnI2 (3.97 g, 12.45 mmol) and sodium cyanoborohydride (3.91, 62.23 mmol). The solution is stirred for 1 hour, filtered thru celite and concentrated. The residue is purified by ISCO column chromatography (5%-10% EtOAc/hexane gradient) furnish the title compound (1.53 g, 5.86 mmol, 71%). 1H NMR (CDCl3), δ 1.69-1.82 (m, 2H), 1.84-1.92 (m, 2H), 2.14 (s, 3H), 2.84-2.98 (m, 1H), 3.49 (dt, J=11.8, 2.2 Hz, 2H), 4.00-4.07 (m, 2H), 6.51 (s, 1H).

Workup

  1. filtrationfiltered thru celite
  2. concentrationconcentrated
  3. customThe residue is purified by ISCO column chromatography (5%-10% EtOAc/hexane gradient)

Sources & evidence

ORD record
ord-2c4e3872110d4308941bb7958569fcf2
Source dataset
uspto-grants-2009_11
Patent number
US07612067B2

Reaction notes

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