Formic Acid → 1083302-30-0

HRID 1363229Notes

Reaction equation

HRID 1363229 reaction equation
C(N(CC)CC)C.C(O)=O.[F:11][C:12]1[CH:21]=[C:20]2[C:15]([CH2:16][CH2:17][CH2:18][C:19]2=[O:22])=[CH:14][CH:13]=1>CN(C=O)C>[F:11][C:12]1[CH:21]=[C:20]2[C:15]([CH2:16][CH2:17][CH2:18][C@@H:19]2[OH:22])=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 284Formic AcidHCID 8471TriethylamineHCID 103747647-Fluoro-1,2,3,4-tetrahydronaphthalen-1-one

Product 1

HCID 282938631083302-30-0Yield 166%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To an ice bath-cooled triethylamine (37.6 mL, 270.5 mmol, 7.4 equiv.) was added drop-wise formic acid (10.4 mL, 270.5 mmol, 7.4 equiv). The reaction solution was stirred at RT for 20 min. 7-Fluoro-3,4-dihydronaphthalen-1(2H)-one (6.0 g, 36.6 mmol, 1 equiv.) and Noyori(S,S) catalyst (560 mg, 2.5 mol %, prepared according to lit. 1, were added. Most was dissolved. DMF (10 mL) was added to make the reaction homogeneous. The reaction turned to dark red and was stirred at 40° C. overnight. TLC was checked and showed no more starting material. The solvents were removed by evaporation. The residue was mixed with water (100 mL) and stirred for 30 min to result a red solid, which was collected on funnel and washed with water and small amount of cold EtOH, then was dried in vacuo overnight. A red solid product (10.1 g, 100%) was obtained. 1H NMR (400 MHz, DMSO-d6) δ 7.16 (dd, 1H), 7.08 (t, 1H), 6.86-6.97 (m, 1H), 5.25 (d, 1H), 4.53 (q, 1H), 2.58-2.67 (m, 2H), 1.82-1.90 (m, 2H), 1.59-1.70 (m, 2H).

Workup

  1. additionwere added
  2. dissolutionMost was dissolved
  3. stirringwas stirred at 40° C. overnight
  4. customThe solvents were removed by evaporation
  5. additionThe residue was mixed with water (100 mL)
  6. stirringstirred for 30 min
  7. customto result a red solid, which
  8. customwas collected on funnel
  9. washwashed with water and small amount of cold EtOH
  10. customwas dried in vacuo overnight

Sources & evidence

ORD record
ord-664370200d034ff38d63dc996805743a
Source dataset
uspto-grants-2011_02
Patent number
US07884109B2

Reaction notes

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