Hexane → HCID 67426543, compound

HRID 1808031Notes

Reaction equation

HRID 1808031 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C@H:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11](=[O:18])[CH2:10][CH2:9]1.CCCCCC.CO[CH:27](OC)[N:28]([CH3:30])[CH3:29]>>[CH3:27][N:28]([CH:30]=[C:10]1[CH2:9][C@@H:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[F:1])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]1=[O:18])[CH3:29]

Participants

4

Reactant 3

HCID 8058HexaneHCID 78373Dimethylformamide dimethyl acetalHCID 59490160HCID 59490160, compound

Product 1

HCID 67426543HCID 67426543, compoundYield 70%

Procedure

A solution of (R)-4-(2-fluorophenyl)-3,4-dihydronaphthalen-1(2H)-one (8.0 g, 33.33 mmol) in N,N-dimethylformamide dimethylacetal (80 mL) was heated at 100° C. for 40 h. After the reaction mixture was cooled to room temperature, hexane (50 mL) was added. Product was collected by filtration and dried under high vacuum overnight to yield the title compound as yellow needles (6.95 g, 70% yield). 1H-NMR (DMSO-d6) δ 7.92 (dd, J=7.2 and 1.6 Hz, 1 H), 7.57 (s, 1 H), 7.42-7.34 (m, 2 H), 7.31-7.21 (m, 2 H), 7.09 (t, 1 H), 6.91-6.88 (m, 2 H), 4.48 (t, J=7.2 Hz, 1 H), 3.25-3.13 (m, 2 H), 3.02 (s, 6 H). LCMS m/e 296 [M+H].

Workup

  1. filtrationProduct was collected by filtration
  2. customdried under high vacuum overnight

Sources & evidence

ORD record
ord-bb870753e48e4615bb400e65156a63cc
Source dataset
uspto-grants-2013_01
Patent number
US08357694B2

Reaction notes

Loading…