Tetrahydrofuran → HCID 66858248, compound

HRID 1803228Notes

Reaction equation

HRID 1803228 reaction equation
[F:1][C:2]([F:15])([F:14])[S:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([OH:13])=[O:12])=[CH:6][CH:5]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].C1COCC1.[Cl:31][CH2:32][CH2:33][CH2:34][CH2:35]I>>[Cl:31][CH2:32][CH2:33][CH2:34][CH2:35][CH:10]([C:7]1[CH:6]=[CH:5][C:4]([S:3][C:2]([F:14])([F:1])[F:15])=[CH:9][CH:8]=1)[C:11]([OH:13])=[O:12]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 825271-Chloro-4-iodobutaneHCID 2724254Sodium bis(trimethylsilyl)amideHCID 27779024-(Trifluoromethylthio)phenylacetic acid

Product 1

HCID 66858248HCID 66858248, compoundYield 47.2%

Procedure

Step AAM (1): 2-(4-(Trifluoromethylthio)phenyl)acetic acid (4.7 g, 19.9 mmol) was deprotonated with NaHMDS 2.0 M in THF (19.9 mL, 39.8 mmol) and reacted with 1-chloro-4-iodobutane (2.44 mL, 19.9 mmol) using a procedure analogous to Step AC (1) to afford 6-chloro-2-(4-(trifluoromethylthio)-phenyl)hexanoic acid (3.07 g, 9.40 mmol, 47% yield) as a pale-yellow oil. LC-MS (M−H)− 325.2. 1H NMR (500 MHz, CHLOROFORM-d) δ ppm 1.32-1.51 (m, 2 H) 1.69-1.87 (m, 3 H) 2.01-2.17 (m, 1 H) 3.49 (t, J=6.56 Hz, 2 H) 3.59 (t, J=7.63 Hz, 1 H) 7.36 (d, J=8.24 Hz, 2 H) 7.61 (d, J=8.24 Hz, 2 H).

Sources & evidence

ORD record
ord-045e712056d14eb58b7781435a0b5dcc
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

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