Sodium borohydride → [(1S)-1-(2-{[tert-Butyl(diphenyl)silyl]oxy}ethyl)-3,4-dihydro-1H-2-benzopyran-6-yl]methanol

HRID 2056759Notes

Reaction equation

HRID 2056759 reaction equation
[Si:1]([O:18][CH2:19][CH2:20][C@H:21]1[C:26]2[CH:27]=[CH:28][C:29]([CH:31]=[O:32])=[CH:30][C:25]=2[CH2:24][CH2:23][O:22]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>C(O)C>[Si:1]([O:18][CH2:19][CH2:20][C@H:21]1[C:26]2[CH:27]=[CH:28][C:29]([CH2:31][OH:32])=[CH:30][C:25]=2[CH2:24][CH2:23][O:22]1)([C:14]([CH3:16])([CH3:17])[CH3:15])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86596016(1S)-1-(2-{[tert-Butyl(diphenyl)silyl]oxy}ethyl)-3,4-dihydro-1H-2-benzopyran-6-carbaldehyde

Product 1

HCID 69310633[(1S)-1-(2-{[tert-Butyl(diphenyl)silyl]oxy}ethyl)-3,4-dihydro-1H-2-benzopyran-6-yl]methanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of (1S)-1-(2-{[tert-butyl(diphenyl)silyl]oxy}ethyl)-3,4-dihydro-1H-2-benzopyran-6-carbaldehyde (0.97 g, 2.18 mmol) in ethanol (30 mL) was added sodium borohydride (0.116 g, 3.06 mmol) and the mixture stirred for 1.5 h at room temperature. The reaction was extracted from water into ethyl acetate, the combined organic extracts dried (MgSO4), filtered and evaporated in vacuo, to yield the title compound as a colourless oil.

Workup

  1. extractionThe reaction was extracted from water into ethyl acetate
  2. dry with materialthe combined organic extracts dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-91f0d5efc46d4c9f8809017e142bf78f
Source dataset
uspto-grants-2008_02
Patent number
US07335660B2

Reaction notes

Loading…