Formic Acid → (R)-4-Chromanol

HRID 1751898Notes

Reaction equation

HRID 1751898 reaction equation
C(N(CC)CC)C.C(O)=O.[O:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14](=[O:21])[CH2:13][CH2:12]1>[Ru]>[O:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C@H:14]([OH:21])[CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 284Formic AcidHCID 8471TriethylamineHCID 68110Chromanone

Product 1

HCID 640695(R)-4-ChromanolYield 100%

Reagents, catalysts & solvents 1

HCID 23950RutheniumCatalyst

Conditions

Temperature
30 °C

Procedure

Argon was introduced into a 20 mL Schlenk-type reaction tube and bathed in an ice bath, then triethyl amine (3.6 mL, 26 mmol), formic acid (1.2 mL, 31 mmol), 4-chromanone (1.48 g, 10 mmol, substrate/catalyst ratio=500) and ruthenium complex RuCl[(R,R)-Tsdpen] (p-cymene) (12.7 mg, 0.02 mmol) were set therein, stirred at 30° C. for 24 hours. On its course, samples were collected after 3 hours for 1HNMR and HPLC analyses of the product. The conversion rate after 3 hours was 66%, and the optical purity was 99% ee. The reaction was allowed to further continue, and after 24 hours, (R)-4-chromanol was produced at 100% yield of and 99% ee optical purity.

Workup

  1. additionArgon was introduced into a 20 mL Schlenk-type reaction tube
  2. custombathed in an ice bath
  3. customOn its course, samples were collected after 3 hours for 1HNMR and HPLC analyses of the product
  4. waitThe conversion rate after 3 hours was
  5. waitafter 24 hours

Sources & evidence

ORD record
ord-8042aae5eb34440bb4dc14d2ba4c396c
Source dataset
uspto-grants-2015_10
Patent number
US09162934B2

Reaction notes

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