Diethyl Ether → HCID 87394252, compound

HRID 918991Notes

Reaction equation

HRID 918991 reaction equation
O1CCCCC1[O:7][CH2:8][C:9]#[C:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24].[CH3:26]COCC>>[OH:7][CH2:8][C:9]#[C:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([O:25][CH3:26])=[O:24]

Participants

3

Reactant 2

HCID 3283Diethyl EtherHCID 67425110HCID 67425110, compound2×

Product 1

HCID 87394252HCID 87394252, compoundYield 83%

Procedure

Concomitant esterification of the carboxylic acid and cleavage of the THP ether in 16-(tetrahydro-2H-pyran-2-yloxy)hexadec-14-ynoic acid (1.0 g, 2.84 mmol) as described above furnished methyl 16-hydroxyhexadec-14-ynoate (665 mg, 83%) as a colorless oil. TLC: 30% EtOAc/hexanes, Rf≈0.40; 1H NMR (CDCl3, 300 MHz) δ 4.22-4.26 (m, 2H), 3.66 (s, 3H), 2.29 (t, 2H, J=7.3 Hz), 2.20 (tt, 2H, J=2.1 Hz, 6.8 Hz), 1.21-1.66 (m, 20H).

Sources & evidence

ORD record
ord-e6ae5bd9f6b2447f9e7083a397485b16
Source dataset
uspto-grants-2016_03
Patent number
US09272991B2

Reaction notes

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