Tetrahydrofuran → HCID 66858742, compound
Reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([OH:12])=[O:11])=[CH:5][CH:4]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].C1COCC1.[Cl:28][CH2:29][CH2:30][CH2:31][CH2:32]I>>[Cl:28][CH2:29][CH2:30][CH2:31][CH2:32][CH:9]([C:6]1[CH:5]=[CH:4][C:3]([S:2][CH3:1])=[CH:8][CH:7]=1)[C:10]([OH:12])=[O:11]Participants
5
Procedure
Step AAL (1): 2-(4-(Methylthio)phenyl)acetic acid (1.00 g, 5.49 mmol) was deprotonated with NaHMDS 2.0 M in THF (5.49 mL, 11.0 mmol) and reacted with 1-chloro-4-iodobutane (0.672 mL, 5.49 mmol) using a procedure analogous to Step AC (1) to afford 6-chloro-2-(4-(methylthio)phenyl)hexanoic acid (1.36 g, 4.99 mmol, 91% yield) as a pale-yellow oil. LC-MS (M−H)− 271.1. 1H NMR (500 MHz, CHLOROFORM-d) δ ppm 8.95 (1 H, br. s.), 7.12-7.28 (4 H, m), 3.39-3.55 (3 H, m), 2.39-2.50 (3 H, m), 1.97-2.19 (1 H, m), 1.59-1.86 (3 H, m), 1.28-1.51 (2 H, m).
Sources & evidence
- ORD record
- ord-528920dda55a4306bfbb8f1577091b13
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08349880B2
Reaction notes
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