Sodium borohydride → (6-iodo-2,3-dihydro-1H-inden-5-yl)methanol

HRID 604613Notes

Reaction equation

HRID 604613 reaction equation
[I:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][CH2:8]2)=[CH:4][C:3]=1[CH:11]=[O:12].[BH4-].[Na+]>CCO>[I:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][CH2:8]2)=[CH:4][C:3]=1[CH2:11][OH:12]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 866261456-Iodoindane-5-carbaldehyde

Product 1

HCID 57576294(6-iodo-2,3-dihydro-1H-inden-5-yl)methanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 6-iodoindane-5-carbaldehyde (35.5 mg, 0.131 mmol) in anhydrous EtOH (3 mL) under N2 at 0° C., was added sodium borohydride (20 mg, 0.522 mmol) as a powder. The mixture was warmed to room temperature and stirred for 0.5 h. The mixture was quenched with water. The aqueous layer was extracted with EtOAc (3×). The combined organic extracts were dried (Na2SO4) and concentrated in vacuo. The residue was purified by flash chromatography (Si, hexanes/EtOAc) to afford (6-iodo-2,3-dihydro-1H-inden-5-yl)methanol. 1H NMR (500 MHz, CDCl3) δ 7.70 (s, 1H), 7.33 (s, 1H), 4.68 (d, J=6.3 Hz, 2H), 2.92-2.88 (m, 4H), 2.12-2.06 (m, 2H), 1.96 (t, J=6.4 Hz, 1H).

Workup

  1. customThe mixture was quenched with water
  2. extractionThe aqueous layer was extracted with EtOAc (3×)
  3. dry with materialThe combined organic extracts were dried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography (Si, hexanes/EtOAc)

Sources & evidence

ORD record
ord-fc547669b44048b79a7f3cbe7b471ccc
Source dataset
uspto-grants-2011_03
Patent number
US07910592B2

Reaction notes

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