1-Iodopropane → HCID 11618793, compound

HRID 1169945Notes

Reaction equation

HRID 1169945 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH2:25][C:26]([OH:28])=[O:27])[CH:12]=[C:13]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=2)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.I[CH2:40][CH2:41][CH3:42]>C1COCC1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:25]([CH2:40][CH2:41][CH3:42])[C:26]([OH:28])=[O:27])[CH:12]=[C:13]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:23])([F:24])[F:22])=[CH:17][CH:16]=2)[CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 336431-IodopropaneHCID 2733832Lithium HexamethyldisilazideHCID 11501912(5-Benzyloxy-4'-trifluoromethyl-biphenyl-3-yl)-acetic acid

Product 1

HCID 11618793HCID 11618793, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-15 °C

Procedure

(5-Benzyloxy-4′-trifluoromethyl-biphenyl-3-yl)-acetic acid (0.09 g, 0.23 mmol) in THF (1.2 ml) was added dropwise to a solution of LHMDS in hexanes (0.49 ml, 0.49 mmol, 1.0M) at −15° C. After 30 min iodopropane (0.08 ml, 0.82 mmol) in THF (0.3 ml) was added and the mixture was stirred for a further 30 min at −15° C. The mixture was then quenched by pouring onto a mixture of ice and HCl solution (2M aq). This was then extracted with EtOAc (×2), washed with NaHSO3 solution (10% aq) and the organics were dried (MgSO4) and then concentrated in vacuo to afford a yellow oil. The oil was purified by flash column chromatography (EtOAc:petroleum ether) to afford 2-(5-benzyloxy-4′-trifluoromethyl-biphenyl-3-yl)-pentanoic acid (0.016 g, 0.04 mmol) in 18% yield. 1H NMR (CDCl3) δ 7.69-7-63 (m, 4H), 7.47-7.42 (m, 2H), 7.40 (t, 2H), 7.35-7.31 (m, 1H), 7.13-7.09 (m, 2H), 7.01-6.99 (m, 1H), 5.11 (s, 2H), 3.63-3.59 (m, 1H), 2.11-2.03 (m, 1H), 1.84-1.75 (m, 1H), 1.36-1.26 (m, 2H) 0.92 (t, 3H); LCMS method (A), (M-H−) 385, RT=4.9 min.

Workup

  1. customThe mixture was then quenched
  2. additionby pouring onto a mixture of ice and HCl solution (2M aq)
  3. extractionThis was then extracted with EtOAc (×2)
  4. washwashed with NaHSO3 solution (10% aq)
  5. dry with materialthe organics were dried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customto afford a yellow oil
  8. customThe oil was purified by flash column chromatography (EtOAc:petroleum ether)

Sources & evidence

ORD record
ord-eeadbe81e8a845fabefa0085b6f5bbaf
Source dataset
uspto-grants-2010_11
Patent number
US07825160B2

Reaction notes

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