Sodium borohydride → 3-(Hydroxymethyl)-5,6,7,8-tetrahydronaphthalen-2-yl trifluoromethanesulfonate

HRID 604645Notes

Reaction equation

HRID 604645 reaction equation
[BH4-].[Na+].[F:3][C:4]([F:22])([F:21])[S:5]([O:8][C:9]1[C:18]([CH:19]=[O:20])=[CH:17][C:16]2[CH2:15][CH2:14][CH2:13][CH2:12][C:11]=2[CH:10]=1)(=[O:7])=[O:6]>CCO.O>[F:21][C:4]([F:3])([F:22])[S:5]([O:8][C:9]1[C:18]([CH2:19][OH:20])=[CH:17][C:16]2[CH2:15][CH2:14][CH2:13][CH2:12][C:11]=2[CH:10]=1)(=[O:6])=[O:7]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 575761993-Formyl-5,6,7,8-tetrahydronaphthalen-2-yl trifluoromethanesulfonate

Product 1

HCID 575762383-(Hydroxymethyl)-5,6,7,8-tetrahydronaphthalen-2-yl trifluoromethanesulfonate

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Sodium borohydride (36.3 mg, 0.959 mmol) was added to a stirred solution of 3-formyl-5,6,7,8-tetrahydronaphthalen-2-yl trifluoromethanesulfonate (98.5 mg, 0.320 mmol) in EtOH (5 mL) at room temperature. The reaction was stirred for 112 h at room temperature. The reaction mixture was diluted with water (20 mL) washed with brine and dried (Na2SO4) then concentrated in vacuo to afford the crude product. This was purified by flash chromatography (Si, 25×160 mm, 0-30% EtOAc in hexanes gradient) to afford 3-(hydroxymethyl)-5,6,7,8-tetrahydronaphthalen-2-yl trifluoromethanesulfonate. Rf=0.49 (20% EtOAc/hexanes). 1H NMR (500 MHz, CDCl3): δ 7.25 (s, 1H); 6.95 (s, 1H); 4.69 (d, J=4.9 Hz, 2H); 2.76 (br s, 4H); 2.25 (t, J=5.4 Hz, 1H); 1.80-1.77 (m, 4H).

Workup

  1. washwashed with brine
  2. dry with materialdried (Na2SO4)
  3. concentrationthen concentrated in vacuo
  4. customto afford the crude product
  5. customThis was purified by flash chromatography (Si, 25×160 mm, 0-30% EtOAc in hexanes gradient)

Sources & evidence

ORD record
ord-aead2d287375451c92274a272fb5d3ec
Source dataset
uspto-grants-2011_03
Patent number
US07910592B2

Reaction notes

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